Hot girl/woman pays nerd/ugly guy for sex

[Strangebuddy]

Wanted to mix things up a bit. An attractive woman with cash to burn finds a guy who is either socially awkward/and or homely and has a proposition for them: they’ll pay them $2000 if they come home with them and let them fuck them for a weekend. The question is: why does the woman insist on paying?

A few rules:
1. Woman is able to get a guy without paying if she wants.
2. The guy is not an escort or sex worker.
3. Woman is not being blackmailed into doing this.
4. She intends to actually fuck him. This isn’t a trick.

So what are some ideas?
1. High schooler about to graduate. Finds a classmate who has an obvious crush on her but never has the balls to approach her. She finds him after class and propositions him. Could be she wants him because of the crush, she does want to fuck someone who is infatuated with her and not just purely lustful like her boyfriend. The money either helps her from getting emotionally involved and also lets her set the terms: she’s in charge. Unlike when boyfriend lays on top of her, she gets to take all the pleasure she wants from the enocounter.

2. Married woman. Husband barely wants sex anymore...so trying to get his attention, she huffily asks if she should get a lover, which he just shrugs and agrees to. So she gets an ugly guy to fuck, paying him so her husband will at least have a financial incentive to start paying her more attention if he isn’t enraged enough to just get back to fucking her. Unfortunately, he’s okay with the arrangement but at least the guy turns out to be a good fuck.

3. It’s a kink and the money only enhances the experience. Essentially, paying for sex: sleazy and hot. Fucking an ugly guy: sleazy and hot. Doing both: holy shit, exponentially hotter.

4. Older woman with neighbors and their sons. Mature woman dreams of seducing virgins or fucking and ugly men. She also has a load of money. So when she hears a woman talk about how her no good son is asking for money for a new computer, she quickly finds a way to make him a proposition. Guy goes broke with his vehicle? She’s already calling him over to seduce him.

 

[Yerkiddin]

Some woman in her 30s decides she wants a smart kid, so she finds a young man with brag-worthy SAT/ACT/whatever scores that just signed up for some brainy university and some fancy major or two. She pays him for sex and for keeping his mouth shut.


Some wealthy woman might bribe some young man whose family has ties either to royalty or big business, in hopes of that man siring a child whose DNA could lead to business merger or some minor nobility.

 

[ThisNameIsntTakenYet]

Slightly different angle, but it could be her job? Like, hot or popular women might get stalked or otherwise receive unwelcome displays of affection from fans/admirers, so they hire her to get the guy's attention away from them? She gets paid handsomely for it, part of which she uses to pay the guy in question. So they get money and sex with an equally (if not more) attractive woman, as long as they promise to leave the women who hired her alone.

The last bit is optional though. Maybe she doesn't tell them to leave the woman they're stalking alone but just tries to distract them and shift their attention onto her instead.

I realize this is a weird story idea, and needs some refinement and proper storytelling to be believable or good. Don't use it as is, but it was a weird thought I had reading this thread and perhaps it might inspire a story.

 

[UsuallyPresent]

I like Taken's twisted take. With enough money almost anything becomes possible.

Now, this could become an 'ugly duckling' type story, where the creep grows up into an attractive, more-than-competent lover.

This could be a scylla & charybdis type scenario - drawn to the original crush and distracted by the other woman. Which way does the guy go with the tug of war? Could end up as kink, or romance, or violence.

A lot of this could end up depending on how the guy learns about the new woman's job. If she falls for him (Pretty Woman/Pygmalion, anyone?) and breaks down and tells him, this could drive him harder at the original woman. This could drive BOTH of them at the other woman - the new woman will do anything for her new lover.

So many interesting options here....

 

[ThisNameIsntTakenYet]

Hmm... Having read UsuallyPresent's comment and thought about it a bit more, I think my idea might work better if it's not the woman's actual job, at least not something she does all the time. Instead, it might be more interesting if the popular woman just goes up to her and goes "hey, want to make a stack of money? See that guy over there? Keep him away from me, I don't care how you do it." That way it's more of a new thing for her, and if the guy's only interest seems to be of a sexual nature, well... if she needs the money badly enough she might let him fuck her if that means she gets paid. (I just realized this basically turns her into a prostitute in a way. That could be an interesting plot point if she realizes that)

 

[UsuallyPresent]

Hmm... Having read UsuallyPresent's comment and thought about it a bit more, I think my idea might work better if it's not the woman's actual job, at least not something she does all the time. Instead, it might be more interesting if the popular woman just goes up to her and goes "hey, want to make a stack of money? See that guy over there? Keep him away from me, I don't care how you do it." That way it's more of a new thing for her, and if the guy's only interest seems to be of a sexual nature, well... if she needs the money badly enough she might let him fuck her if that means she gets paid. (I just realized this basically turns her into a prostitute in a way. That could be an interesting plot point if she realizes that)

The real job here is a third person in the middle of the above - the procurer, the person who finds the distraction and gets them (money? blackmail? kink? professional advantage? lots of options HOW they get the new woman involved) to distract the determined but unwanted guy.

Could be a series on how this procurer does their job, servicing the needs of the wealthy and powerful to separate distractions from those they wish.

IF you wanted to go evil with the tale, the procurer's job could include breaking up happy, committed couples so a third party has a shot at rebound sex/relationships with one of the couple.

Bonus points if there's no mysticism, just personal charisma, business acumen, and manipulative skill.