Matchmaker winds up in a threeway

[Brandnewbuddy]

So originally I had a more specific idea (which I’ll share in a bit) but I’d like to see other people’s take on the general premise.

Premise: stories about someone trying to play matchmaker between two people winds up in a threeway with them.

For example: Cheerleader hears nerdy girl or guy moaning about how they can’t get a girlfriend/boyfriend, maybe nerd is a step sibling, classmate, what have you. So wanting to get stick her nose in things or maybe get some financial compensation from the nerd or nerd’s relative, she sets to hook them up with another nerd. Only thing is, both of them are socially awkward as hell so cheerleader has to go on “practice dates” with both of them to get them to be okay with the idea.

So the night of the first real date occurs and both of them really hit it off and they even want to go all the way, cheerleader is delighted, and then she has both of her hands taken and she’s guided up to a bedroom: turns out the nerds really liked the practice dates and have fallen for her and each other. Well…she doesn’t want this date to fail, does she?

Example 2: Mom’s friend finds out mom’s son is single and so is their neighbor’s daughter. Mom’s friedmnd sets about hooking them up, gets to know them and even finds out they’re both Bi and have only had boyfriends before (a secret son kept from his mom), she keeps it a secret but after a few good dates, they invite the friend up: daughter feels mom’s son is her one true love but she wants to try a woman at least once before she commits and son has never been with a woman so he’s worried about givining his girlfriend a bad first time with him, so they want friend to help them out.

 

[DarkSollat]

Both delightful ideas!

In Example 1 I'd however keep the cheerleader as dominant. So the date is going well, but nerds're too shy to make a move toward each other, and then don't really know what to do, so the cheerleader needs to show them how to kiss, how to touch, how to fuck.

 

[Carnevil9]

Both delightful ideas!

In Example 1 I'd however keep the cheerleader as dominant. So the date is going well, but nerds're too shy to make a move toward each other, and then don't really know what to do, so the cheerleader needs to show them how to kiss, how to touch, how to fuck.

I love it! You could even make the cheerleader the sister of one of the nerds to give it an incest angle, or an older person to give it a mature angle.

 

[DarkSollat]

I love it! You could even make the cheerleader the sister of one of the nerds to give it an incest angle, or an older person to give it a mature angle.

Older person cheerleader? XD

 

[FantasySharer1]

I love it! You could even make the cheerleader the sister of one of the nerds to give it an incest angle, or an older person to give it a mature angle.

Love the incest angle. Maybe the sister is setting up her nerdy brother with her nice friend and they are both too shy. So she gets them to relax and eventually ends up putting her brother's MASSIVE cock into her friend's pussy with her own hands.

Her friend cums HARD after a light fucking because she's a virgin and he filled every corner of her. Brother is still aroused and has blue balls and an eight-inch erection and doesn't know what to do. Sister takes over and slides him into herself and gets pounded by her brother.

Their lives change forever.

 

[Brandnewbuddy]

You know I was going to not do a taboo angle but if they are nerds, especially otaku, I could see some jokes about it.

“Whoa…hold on there dude. Kissing is one thing, showing you a trick or two on your new girlfriend is a stretch, but actually fucking you? I’m your sister!”

“Older sister” I suddenly heard and turned to face the girl who I had roped into being my brother’s date. Her eyes were practically devouring me through her thick lenses. Her tongue sat perched atop her bottom lip as each heavy pant pushed a bead of drool down into a slow stream. She looked like a hyena who had found an abandoned carcass and turning back to my brother, I saw the exact same expectant look.

Then it hit me: these were two anime loving, body pillow humping, hentai torrenting. erotic doujin reading Otaku…and I had put them in the same room as an attractive older sister with the intent of getting them to lose their virginity.

…I had greatly miscalculated.

As I stared at the lust crazed basement dwellers who were already working off their last shreds of clothes as they watched me consider my position, I could only form one sentence before I relented and shed my top:

“If either of you call me ‘onee-chan,’ we are fucking done.”

 

[Brandnewbuddy]

…okay now I’m actually pretty tempted to write it, but as full on comedy where the cheerleader is just as big of a dork as her sibling just not a nerd.

Like she ends up having to be the one to take her brother’s briefs off and once his cock springs out she says “nice”:

“Only, it wasn’t a sexy ‘nice.’ There was no melodic lengthening of the ‘I’ coupled with a suggestive flexing of the brow and an enticing smile capped off with a sudden licking of the lips. It was not even a breathy ‘nice’ that came off a warm moan and exited the mouth with a breath that would reach out to the top of his cock and transform into a shiver that that would travel down his shaft and then explode across his nervous system, reducing him to a shivering mess of anticipation.”

“I had said “Nice” like like my dad would say when his friend showed off lawnmower, I had said “nice” like my first boyfriend when he saw a muscle car that he thought was cool but not that cool. I had said nice like when my uncle was appraising a catfish I had caught. It was a cordial, curt, and courteous “nice.” But it was definitely by no means a sexy “nice” nor was it an appropriate nice for complimenting my brother’s cock (…okay not sure what an appropriate “nice” would be for that but still). And as if it wasn’t bad enough, I watched in horror as my right hand contorted into a thumbs up, which I held up proudly like some old politician.

“…yes, it’s…nice.” I heard his girlfriend say before she mimicked me and also thrust forth a thumbs up.

“Don’t encourage me, you idiot!”

 

[CuttingEdge]

The real life story of Gary Kremen comes to mind here.

The guy took out a $2500 advance on his credit card when only 5% of Americans had internet, and started Match.Com. That was great until his wife left him.... having found her soulmate on Match.Com.

There has got to be an erotic story within that somewhere!

 

[Brandnewbuddy]

Another idea: guy has a friend who he thinks is a lesbian. He sees her checking a girl out but when it looks like she’s going to ask her out she chickens out. Deciding to help her, he starts motivating her while also befriending her crush. He gets the two together and they invite him on their first date…turns out everyone misread the situation: friend and her crush are bi and poly, and they want to be a throuple

On the flip side, woman helps two two guys out and winds up in MFM sandwich