“Please fuck my friend”

Brandnewbuddy

Literotica Guru
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Sister comes to brother with an odd request: she needs him to go on a date with her friend and fuck her.

Brother is taken aback. Sister’s friend isn’t unattractive (not necessarily gorgeous but definitely not ugly) and seems like she could get a man if she wanted. Also, why is his sister asking him? Seems strange but he doesn’t have anything going on at the moment so why not?


Once again, I think I’ll let you all discuss what would be the most interesting turn of events. Brother could be older or younger or a twin and the reason for sister asking could be anything from comedic (she’s just so…so tired of her friend whining about not getting laid) to blackmail (“your brother fucks me or I spill the beans about “x”), horror, or any genre really.
 
Yeah, I don't think there's an eighteen year old that wouldn't jump at the chance to fuck his sisters friends.

Now, does the sister want to watch? I know, a little kinky, yet she is asking him to plow her fields.

Maybe the sister want's to participate? Same as above.
 
Lol, no, brother is up for it. He might have questions and be suspicious but he’s down for it in every scenario.

Sister wanting to join in could be an interesting path for the story to take. One idea I had was that Sister is so desperate to get her friend laid that she starts throwing out offers before he has a chance to even respond (once again, he’s up for it, he just needs a moment to process it).

For example:

“Look, I get it you don’t have that much experience, worried you’ll shoot your shot too early. I get that. How about we work on that? Handjob, blowjob,”

“What?!”

“No, I got you, if we’re going to break the law may as well go all the way. How about a trip around the world, no stops, courtesy of your desperate sister. For the love of god just please fuck Becky!”

“Yes! Sure! Okay!”
 
My mind drifted to the friend got laid by two different guys and still is not sure what an orgasm is.
Brother is excited to help as long as sister comes along to assist. Somehow write it to be sensual and brother and sister team up and make her friend cum during foreplay. Brother gets laid and sisters friend is curious about her pussy too. In real life I was in my 20's she was in her 30's I gave her her first orgasm. The threesome that almost happened all started with her divorced friend a bit tipsy saying "her ex was an asshole but he could lick me to like never ending orgasms, I need to cum" The lady I ended up with responded with a "what?" We explained a bit and she was very interested. At that point her friend left. I so wanted to demonstrate....
Anyway it comes out I'd read your story. And not just for the incest. I like the frst time kind of innocence. So many times I have taken time to get a woman into bed only to find she was only ever used. Find a woman's orgasm you get good sex for life. Find your own and leave her wet and needy you create a bitch with a bad attitude.
 
Sister comes to brother with an odd request: she needs him to go on a date with her friend and fuck her.

Brother is taken aback. Sister’s friend isn’t unattractive (not necessarily gorgeous but definitely not ugly) and seems like she could get a man if she wanted. Also, why is his sister asking him? Seems strange but he doesn’t have anything going on at the moment so why not?


Once again, I think I’ll let you all discuss what would be the most interesting turn of events. Brother could be older or younger or a twin and the reason for sister asking could be anything from comedic (she’s just so…so tired of her friend whining about not getting laid) to blackmail (“your brother fucks me or I spill the beans about “x”), horror, or any genre really.


I like the concept. Some of these ideas can work. Maybe the sister is tired of her friend complaining about not finding a man, but instead of blackmailing her brother she has something to offer him to sleep with her friend, like tickets to a game or she'll do his college homework, things like that. Blackmail seems overly done in these websites, bribery could work if she had something good to offer him. Also, if she's still a good looking girl, it will make it easier for him to take the bribe just to get laid.



....
 
How do you see the story ending? With a tasty fuckoff by the bro? With bro and sis's BFF hooking up long-term? Does sis have other BFFs who need fucking? Is bro up to the task? (Maybe he's mostly gay and needs special enticements.) 2-ways or 3-ways or more-ways? Do tentacles intrude?
 
It might be more realistic if the friend went through a bad breakup and isn't feeling that great about herself with low self-esteem. The sister wants her brother to meet them out and compliment her and make her feel good without "taking advantage" of her in her state of mind. Things go a little differently with the brother fucking the friend. The sister is pissed off at the brother but he ends up fucking the friend again.

Let me know if you want to collaborate on the story.
 
THE SISTER's FRIEND is a friend from college in town for s weekend long business convention.

THE SISTER's FRIEND will be engaged with daily and nightly activities until Sunday night before she leaves the following AM.

THE SISTER's FRIEND is rising star in an industry dominated by men as she has a voracious appetite for money, success and the deal. This determination stems from a patterned behavior emanating form high school and blossoming to obsessive proportions in college.

THE SISTER's FRIEND was a predator that sexually consumed her prey while looking for her next victim.

THE SISTER knew that THE FRIEND would feed upon all the sex-starved husbands populating the convention halls, business dinners and rooms accessed by keys held out by unsuspecting suburban feeder fish.

STILL

THE SISTER wanted to see THE FRIEND and take her out to the favorite local eatery that she had been raving about for years. THE SISTER's fiance would treat the FRIEND to this Michelin restaurant with the promise of an escort for dancing.

THE SISTER even though she was engaged did not trust THE FRIEND so she called upon the sexual bravado of her kid brother to dine, dance and distract THE FRIEND.

THE SISTER promised the friend a date while promising the kid brother a sure thing along with the caveat that he document all that occurs behind her closed door. Video. Audio. Testimony or a police report that would help turn gray rumors into black and white.

A matter of quelling the sister's curiosity that could very well kill the kid.
 
How do you see the story ending? With a tasty fuckoff by the bro? With bro and sis's BFF hooking up long-term? Does sis have other BFFs who need fucking? Is bro up to the task? (Maybe he's mostly gay and needs special enticements.) 2-ways or 3-ways or more-ways? Do tentacles intrude?

A few possibilities I thought of:

1. Bro is happy to help and leaps at the chance…only to find out that there’s a good reason friend isn’t getting any action: she’s utterly insufferable. To a comical degree he keeps losing interest and regaining it even as they head upstairs.

Does a striptease: he’s interested.
Starts badmouthing his sister: not interested
Gives him a lap dance: he’s interested
Decides to share her conspiracy theories: not interested.
Starts kissing him: very interested
Starts laughing with with the most nasally snort: oh god.

2. Brother agrees but then has to dance around friend’s suspicions that he’s here to give her a pity fuck (even though he’s interested, she still thinks he’s only doing it because his sister asked him…which is partially true).

3. The night goes well…then friend’s boyfriend shows up. Yeah, sis left out that she was trying to get friend to realize there were other, nicer guys out there and she didn’t have to stick with the first guy she had sex with. Fortunately, friend does take it to heart…unfortunately bro is pantsless with a ticked off alpha-douche trying to break in.

4. Sis left out the fact that friend turns into a sex demon if she doesn’t get laid in a certain time and bro’s slight hesitation makes the clock tick down and the gorgeous woman he was making out with is now a tendril beast that is just as horny but isn’t as safe to be around.

5. Bro is older by over 10 years. And friend has a taste for older men. Bro is a bit reluctant since he looks old enough to be friends dad. Sister knows this and is hoping that bro will be classy enough to not take advantage of friend past a one night stand or maybe a little more.

I figure with most endings bro and friend get what they want (or at least friend does) and then head their separate ways, though they could be a couple.

I will admit for most ideas I figure sis doesn’t get involved except for the start and maybe some phone calls when the shit hits the fan, though I could see one or two stories where she plays a more active role (like the last one I could see bro setting friend on the right path but doesn’t sleep with her…sis pulls him aside afterwards and decides to thank him for being a decent guy..with some indecent fun).
 
The sister and the Best Friend have a bet: who can go the longest without having sex. The stakes are really high and the sister really, really wants to win. She knows that her brother is a world-class cocksman and figures if he takes out the Best Friend, he will surely seduce her and the sister will win the bet.

Of course, for a good story, nothing can ever go according to plan.
 
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