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So this is an older story but it was the first one that popped into mind and felt the need to share. It's not as wild as some of the stories here, but for me at the time it was pretty great. Here it goes.
I dated my ex for about 2 years after having been friends with her since we were 13. Let's say her name is Alli. Alli has a an identical twin sister who we'll call Emily. So Alli is an attractive girl long light brown curly hair, green eyes, and pretty curvy but still felt somewhat petite. Her sister as you can imagine looked identical but had shorter blonde hair and usually kept it straight. Now as I've said I have been friends with these girls since I was a young kid and so every once in a while our group of friends would dabble in spin-the bottle type of games. Nothing serious or anything just making out and exposing body parts. So I used to partake in these kinds of things with both Alli and Emily, and it was never awkward or anything just some good old sexy fun. (This backstory is relevant, but I will move on as to not push my limits with the sub rules).
Anyways needless to say once I grew up, I eventually started dating Alli for a couple of years. We were each others first. Now I don't know if anyone has ever had this feeling, and this goes for anyone who has ever dated a twin before, but every once in a while you kind of get this feeling that you want to fuck the twin sister of the girl/guy you are dating. Even though physically they look exactly alike something inside you imagines that you are fucking someone else. It's hard to explain but it would always get me off.
So one day closer to the end of our relationship, I went up to her Uncles cottage with her family. The sleeping arrangements were the four of us Alli, Emily her boyfriend and myself on air mattresses, in the basement all in the same room. Emily and her boyfriend had been dating for so many years that I guess they did not feel the need to sleep together so he slept on the couch behind us and Emily slept alone on one single person mattress, while I shared the double with Alli. The mattresses were basically pushed right together and I found myself sleeping between the twin.
So that night especially there must have been something in the air because Alli had never been that adventurous sexually in the 2+ years that we dated, so compared to our usual sex this was closer to a porno. We went to bed that night all at around the same time. It was fucking hot down there at night. No one was really sleeping with a lot of blankets, and I remember looking over at Emily and noticing her little pyjama short were riding up her ass as she slept, and the wet sweaty tank top she was wearing curved the outline of her nipples. So I watched her for a bit and felt Alli behind me moving to come spoon me. She immediately began thrusting into me and I could feel the heat from her pantie area pushing against me. She reached over and grabbed my cock which was half hard from sitting there staring at Emily's ass just imagining pulling her shorts to the side and sticking my dick so far up her pussy. So Alli kept pushing her pussy up against my back and I eventually turned to face her, we made out and she kept stroking my cock. I eventually tried to return the favour but she would not let me. She continued to tease me and eventually started going down on me. I was obviously ready to go but I felt like already we were getting super loud and there was her sister sleeping right next to me. She started sucking my dick, licking my balls and doing all these things she wouldn't usually do with my dick in her mouth. She eventually came back up and turned to a spoon position. She pulled down her panties and stuck her ass against my dick and told me to play with it. I reached around for her pussy and felt it dripping wet without even having to stick a finger inside. She quickly grabbed my hand and said not there and moved my hand around the other side and towards her asshole. It had been recently waxed clean, something I had never experienced before. She would never let me venture there but in the heat of the moment I guess she was feeling adventurous. She laid down flat on her stomach as I slowly tickled the rim of her asshole. Her legs were spread with her ass sticking up in the air, and I resumed a position to make it look like I was somewhat asleep. I eventually poked a finger through and felt her insides, she quietly moaned and I continued to play with this new hole, I eventually stuck another finger in her pussy and began playing with the soaking wet combo. Eventually she turned over, and I'll never forget this. She whispered in my ear "fuck me as if you were fucking my sister" I almost blew right there. I laid her down, face in the pillow ass up and stuck it so deep in her. I was at the point where I didn't give a shit if anyone woke up. Needless to say she came almost immanently. She had this thing where she could come almost right away, it was great (soon did I realize not all girls are like that). I could hear her hold in her cries but I felt myself coming close also. I looked at her face staring at her sister, making moaning faces, there was Emily just lying there fast asleep or too revolted to open her eyes and face the sounds. I stared over at her sleeping there once again focusing on the tight wet tank top and nipples sticking through. I let it go and came deep inside of her. She turned onto her back and did something I've never seen her do. She reached down stuck a finger between her legs, drew my cum out of her pussy and traced it up along her stomach, past her hard nipples and onto her lip where she licked it clean.
I went to bed in shock at what had occurred that night. We never really brought it up again after that.

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