Big sis to the rescue

Reshbod

Literotica Guru
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Somewhat based on a true story where an awkward boy has trouble making friends and is often by himself while his sister is very outgoing and popular. Both are attending the same college with the boy being a freshman and the sister being perhaps a junior or in her final semester.

She tries to help him get out and experience life and he is not interested since she is his sister. His friends or more accurately acquaintances push him to get with her not knowing they are related. They arrange things so that he and his sister end up together for a "date". He plays along while the sister tries to help him come out of his shell.

They eventually become lovers but I'm not sure how they get from point A to point Z. This type of story has been done many times but I want to avoid the usual cliches. any comments or suggestions would be appreciated.
 
I would approach it from the other way around entirely. Starting outright with the bro and sis having an extremely close, but strictly non-sexual relationship.

Maybe they had shared room some time in childhood, maybe just very good siblings. Mabe that's his sister's nature, being three years younger he's been one of her dolls to play with, and it grow out from there. They have little to no modesty between them, have no hesitation to change clothes in front of each other, skinny dipping together (it's even possible she only ever does that with him), sit in sauna together, maybe even have had showers together on some occasions. However, there's very fine, but very definite lines they never crossed. By now those boundaries could be in unchanged effect for fifteen years.

It's reflected also in language, he's knowing everything about her love life, as in, relationships, but no truly intimate details. Had her date had a happy ending has to be infered from circumstantial claims and double entendres. Well, if it goes truly sideways, it's the bro who rides to the rescue. And he have had to salvage her after a near rape too. All since he grew up to over six feet at sixteen, he's been the proverbial man with the shotgun sister's failed suitors had to turn around from. They have a father, and he's great guy, but he doesn't know more than a tenth of daughter's escapades, while bro can extrapolate the one tenth he's missing. Mom knows nothing at all, and shouldn't, or she would have a neurotic breakdown.

The brother, he's not that innocent either. Perhaps he had a stable (innocent) girlfriend through most of high school, just to have an ugly breakup in the middle of the senior year. He had then used his unsought freedom for a little series of quick conquests or near conquests, some of with might have been very gratifying in the moment, but in the aggregate already left him resentful. And that's what bother the sister actually, that bro could have any girl he wants if he would be more outgoing, but he's growing into an incel, or so she's afraid in her fast and exaggerated ways. The truth may be, she may have overmanaged some of those bro's quicky girlfriends the past summer, been way too intrusive already.

And unlike sis to him, he's not telling half of what's going in his head to her. He may actually even be in a slow long distance relationship, may not see it as serious either, but that's it for him at the moment, and he's actually content with that. The girls the sis is trying to acquaintance him with, well, they're either her friends who's are all older, still "too old" or the type of younger girl he's subconsciously recognize as "sluts" and has already burned at that, so not interested in more of that for now. The main disconnect here is, the bro has long term thinking, he's evaluating a girl as mother of his children first, a quick fuck secondary (and yes, that's a strategy likely bound to fail in the modern world), while the sis lives in the moment.

Okay, but if we want the siblings to break the block and fuck finally... the way to get there is to get the sister seriously jealous at bro's next girlfriend. Perhaps, not by small part because having lust for her herself too. And yes, I would end it at a triad, with a hint it won't last, but in whatever way it breaks the guy coming out with newfound confidence.
 
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And that's what bother the sister actually, that bro could have any girl he wants if he would be more outgoing, but he's growing into an incel, or so she's afraid in her fast and exaggerated ways. The truth may be, she may have overmanaged some of those bro's quicky girlfriends the past summer, been way too intrusive already.

The idea of him being or becoming an intel is intriguing. After his breakup with the high school sweetheart he falls into "girls don't want nice guys" thing. He watches videos and gets more extreme while his sister is everything he begins to complain about, but since she's his sister he doesn't really see it or at least ignores it.

Sister sees where he is heading and tries to stop him. She has a serious boyfriend but spends more and more time with her brother. I also like that the brother starts coming around and leaves the "manosphere" and starts getting close to another woman which causes the sister jealousy and she works against the relationship.
 
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