HS Friends, mid-20s roommates, lifetime secret keepers (MFMF, light incest CF/CF) Prologue | 2016

long time reader, first time poster:

alright so there's going to be a lot of background leading up to the juicy bits so if all you care about is the night it all went down you might as well wait until the second post. I'll try to break it up that way in a horrible sell out to get as many upvotes as possible.

p.s. this is a true story but please don't ask for pictures or any other type of proof. Any pictures of us together are probably on fb or instagram and while this story would make me and my other male friend look great it would not go well for the females involved...especially with their families. I'm simply telling this story to finally get it off my chest and given the things that happened and the fact we have a similar circle of friends I can't exactly go telling it on the nearest hilltop. she's happily married now to a great guy but he's the type who would rather not know anything about her sexual past.

Background:

Olivia (Liv) was one of my closest friends at the time of the hookup. She dated one of my best friends in high school but her group of GFs were always hanging out with my group of guy friends before and after their relationship so I never saw her as my best friend's girl.

Liv is one of those girls who was rail thin growing up but then developed curves in ALL the right places when she went off to college. I personally like a skinnier androgynous-lite girl but I'll be the first to say Liv's body was built for fucking. About 5'5" with brunette/blonde shoulder length hair with a longer, athletic torso, B or C cup breasts (with perfect nipples) and a rear that would make any butt guy thank a higher power. Picturing her ass spilling out of ultra low rise jeans still gets me weak in the knees. More of a strong athletic derrière compared to a Kim Kardashian bomb. For the 1-2 girls who might read this if you're interested in how I look I'll answer in the comments. Otherwise feel free to imagine me as anyone you'd prefer.

Like some girls who went from rail thin to maybe needing to lose a couple pounds (which she eventually did) she had some self esteem issues through college. Coupled with a strong sex drive (I later found out she had at least 30 partners by her mid-20s) and our close relationship she was the perfect girl to flirt with. We went to different colleges but usually hung out on breaks. One game she loved playing while we were together was sticking her hand down the back of my pants and grabbing a hand full of ass. Usually when I was talking with someone else. I would tag her back and it was an extra thrill because sometimes she'd be wearing a very skimpy thong or nothing at all underneath.

Fast forward about five years and we've been living together for a couple years (not as a couple. just friends who enjoyed each others' company). We had a couple drunk make out sessions but to be honest neither of us were the others' type so it never went anywhere. Her ex was living in town for a law firm clerkship and had a thing for Liv's stepsister, Chelsea, so one day we all went out to get drinks. Liv brought a date Chelsea had hooked her up with but Liv then proceeded to get black out drunk. The date wanted to take Liv home but we weren't having that and since the three of us wanted to keep the party going we stumbled Liv on over to the next bar where her date went home and things got...interesting. We were all pretty drunk at this point and Chelsea (basically a skinnier/blonder version of Liv, if you didn't know any better you would say they were actual sisters. probably why my friend was so into her) was doing her best to keep black out Liv from falling asleep in the booth. You always knew when Liv was blacked out because she had this glazed over look in her eyes and perpetually halfway to falling asleep. With Chelsea holding Liv's face in her hands and staring into her eyes, Chelsea did something very unexpected. She leaned in and planted a very long very soft kiss on her lips. Liv didn't pull back but to my surprise opened her mouth and started the sexiest tongue battle with Chelsea, her own stepsister. It only lasted half a minute at most but the image was seared into my brain. And it seemed to do the trick with Liv. She was a lot more alert after that and when my friend and Chelsea were on the dance floor and Liv and I were in the booth alone she did something she had never done before. My dick was still half hard from what I saw and Liv must've noticed because without warning she just grabs it through my pants and looks at me. I could tell she was still blacked out and just kinda scooted away. I would've loved to have been her fuck buddy that night but not when she had no idea what she was doing. She got the idea because she went roaming for cock and gladly she didn't find what she wanted. We all went home sexually frustrated that night (Chelsea decided to walk home alone that night as well leaving my friend with his dick in his hands).

Little did I know that a year later Liv and I would be with her cousin and another friend of mine and this time she wouldn't be blacked out and no one was going home sexually frustrated...