Long time lurker time, first-time poster.
So a bit of background on myself. I’m from the US and originally from South Asia. I grew up a relatively Asian life with good grades, being bad at sports, and always lacking in the women’s department. Around when I was 10 I became really good best friends with a guy who was in the same school as me. Unfortunately, he moved away a year or so later but our parents became good friends so we would always meet up all the time and our families started to get closer. He had one older sister who would always hang out with us since I had 1 older sister as well and the 4 of us hung out all the time. I never really had any sort of feelings for her in that way and honestly, we were so young that I didn’t even think about it.
A bit of time goes by and I get caught up trying to get to college so I’m disconnected from them and behold like 3 years later when we meet up she has completely changed. She is ridiculously hot and I cannot stop thinking about her. At that time I was already talking to someone so I decided I wouldn’t pursue anything and it being my best friend of so long sister I didn’t think I had a chance.
3 months later from then we decide to go on a vacation, I’m in because of my best friend and the family sends us a few hours away to a cabin in the forests and it’s just the 4 of us. The Cabin has this outdoor hot tub and we all decide to get in it and have a few drinks(I know the drinking age is 21, but literally no one ever follows it, I’d started drinking 2 years before that.) We decide to play a game of truth or dare and here are where things start going crazy.
The game becomes just all truth because no one wanted to do anymore dares. As the drinks add up the questions become more persona; but usually between the same genders, so me asking my best friends or my sister asking the girl. Then randomly she poses me a question “Are you a Virgin?”, now usually I would lie fro clout but I was pretty tipsy so I answer truthfully yes. A few rounds later again she asks “Would you want to get with a brown girl or a white girl?”. At that point, I had only ever talked with white women cause of where we lived and so everyone thought I only liked white women, but staring right into her eyes I say, brown girl. The game continues and questions get more personal but we are both locked into each other’s eyes at this point and she starts to play with my foot beneath the water and her feet are in my shorts in a few minutes. I start rubbing her thighs with my feet and things are extremely hot. But there are still two other people in the hot tub.
We decide to get out and go to bed since it’s getting late. We all have our own rooms so we all head off to bed. 20 minutes later I hear a knock on my room and guess who it is. She comes into my room and is like I can’t go to sleep, and everyone else is asleep, can we talk. I say sure and we start talking about random things and then I bring up the hot tub. Now in our culture, it is super taboo to have any relationship with your friend’s sisters. they are supposed to be like sisters to you. She says she’s never been with a guy but she’s never felt attracted to one more than me, but it’s wrong because I’m her brother’s friend so I’m a brother basically. Things are super tense and there is a weird energy building.
Eventually, she reaches in and puts a hand on my thigh and we start making out passionately. I could tell it was her first time as I had kissed before plenty of times, it was super sloppy with her but amazing still. I start moving from her lips down her amazing brown body. Going to her neck and she slightly starts to moan. Now, this is my first time so I’m just trying to remember everything I’ve learned from p**n and since she starts breathing heavy I think to myself that I’m probably doing something right. I move from her neck to her huge boobs, they have to be at least C’s, I take her bra off and just start going crazy licking her tits. I then reach into her pants while I’m still focused on her boobs and with one finger I enter. My finger and palm immediately become soaked. She is so wet but so tight at the same time, my mind doesn’t know what to do. She lets off an insane moan and I look up at her and she is just looking at the ceiling and probably has no clue where she is being in so much pleasure.
I move down by taking her pants off and start trying to eat her out the best I can. All my knowledge from anything I’ve ever learned. She is still softly moaning so I keep going. Then eventually it gets louder and louder and about 3-4 minutes later she lets out the loudest moan yet and I feel her cum all over my face and she almost squirts a bit. I look up to her and tell her she’ll need to quiet down or her brother will come in here and beat my ass. I start about to go down again and she closes her legs. She then starts crying and starts going on about how wrong she felt. My complete hard-on goes away instantly and now I’m there consoling her while she’s completely naked. She says she wouldn’t like to continue anymore so I don’t pressure her at all and start helping her get dressed. She stops before leaving and gives me the biggest smooch ever on my cheek and I just lay there horny af, thinking about what I might’ve done wrong.
Turns out I didn’t do anything wrong but she was just super lost in everything and when she realized it all in the brief moment we stopped she realized how wrong it was with me like being like a little brother. Funnily enough, we end up actually getting together a few months later but this post is already super long so I won’t write that here but let me know if I should continue and share the story of how we both actually lost our virginity.
Source: reddit.com/r/gonewildstories/comments/mk0ice/my_first_time_with_my_best_friends_sister_who_was