Sugar Daddy’s requests

[Strangebuddy]

Thought it would be interesting to see a story about a young woman who has been seeing a sugar daddy. Guys older but up till now he hasn’t requested anything out of the norm: send him some sexy pics during the day, be available to attend functions with him, and of course spend the night with him.

However, he lately has become a bit distant. Worried about him, or at least her source of money drying up, she asks him what’s wrong and he admits he’s been wanting to try something new with her or ask her to do something...but he’s not sure she would be interested (depending on the relationship it could be an obvious attempt to manipulate her and he could mention trying to find a girl who would do the request...or he could genuinely worry about testing her limits)

Woman asks what the request is, and ultimately decides that even if it’s weird, she’ll go through with it.

So the story is about what the request is, the woman going through with it, and where things go from there.

There’s no real hard rules for what the request is aside from literotica’s default rules. Though it should be something that she would be willing to do for money.

For example:
1. Something more tame might be bondage, of her or him. With her, it’s about her boundaries being tested, with him it’s about her balancing properly dominating him while also not going too far.

2. Letting him bet her at a poker night at his place. The guests have to obey the limits she has with him but being shared around by a bunch of guys is certainly a change for her.

3. Being a proxy for sugar daddy. One of the more extreme ones. Sugar daddy has someone he wants to fuck but his position makes it impossible or the person isn’t willing to do it with him no matter the amount of money. For example: secretary is gorgeous but fucking her woudo not only be against company policy but also she isn’t into men. So woman will go seduce her and tell sugar daddy about the entire experience in as much detail as possible.

Of course it could lead into taboo as well. Sugar daddy’s daughter or even granddaughter are gorgeous women. Even if it was only by proxy, he is obsessed with the idea of fucking them. For added touch, woman could go fuck them and harmed them eat her out mere minutes after she has sugar daddy cum inside of her.

Those are just some ideas. The story would be from the woman’s perspective and how she feels doing them. What are some other ideas you can think of?

 

[LupusDei]

3. Being a proxy for sugar daddy. One of the more extreme ones. Sugar daddy has someone he wants to fuck but his position makes it impossible or the person isn’t willing to do it with him no matter the amount of money. For example: secretary is gorgeous but fucking her woudo not only be against company policy but also she isn’t into men. So woman will go seduce her and tell sugar daddy about the entire experience in as much detail as possible.

Of course it could lead into taboo as well. Sugar daddy’s daughter or even granddaughter are gorgeous women. Even if it was only by proxy, he is obsessed with the idea of fucking them. For added touch, woman could go fuck them and harmed them eat her out mere minutes after she has sugar daddy cum inside of her.

What seems obvious for me in this case is to arrange it so that he can secretly watch, or at least for her to take it all on video.

On that theme, there could be even request to carry camera into women's changing rooms or some such. May seem tame sexually, but illegal and amoral.

Going the next step, video her sex with a man he pointed out, for blackmail purposes. She may not know the final goal, it may be presented just as a kink to see her being fucked.

Then there's possibility to outright sell her. He's affluent man and not interested in simple pimping, but there might be circumstances, such as finishing a huge deal, where the implied price of the encounter goes into millions. Perhaps, while with the old money monkey she additionally have to pretend to be sugar daddy's daughter. For that to work more convincingly, she have to meet and study the daughter, including sex... and of course under close supervision by the daddy.

 

[Lost_Yonder]

other scenarios:

- seduce his wife so that she will accept her into the family; though like the idea of getting her to seduce his own daughter - but then setting it up so he "catches" them, seeing what his daughter will do when the sugarbaby invites him to join them
- he has his eyes on another married woman and figures setting up a "swinging"/swap with her and her husband would be the best way to get to fuck her, allowing the other guy to fuck his sugarbaby
- though I do also like LupusDei's suggestion - use her to get to another guy to blackmail
- rather than betting her at poker night, have her be the server, or perhaps for the Super Bowl, with a bunch of friends over, he wants to show her off - have her wear a sexy cheerleading outfit - the intent is just to show her off, but things get out of hand
- maybe he has bi-tendencies and wants to include a young guy and having her participate makes it that much more acceptable to him as he struggles with the idea

 

[Strangebuddy]

Interesting ideas all around.

I like the thought of him using her for professional means. Either closing deals, or getting blackmail material. Could be some drama since having sex for money is one thing but fucking to help someone else make money feels off.

Her pretending to be his daughter gives me a bit of an idea:

Maybe he tells her he needs to get into a “daddy daughter” party. A lot of people he knows will be there, bringing their privileged grown daughters or stepdaughter there to share and fuck them away from prying eyes. She will need to act the part and fuck him knowing actual incest is going on right next to her.

Could either be real or a joke he’s playing on her. It could be all the “daughters” are sugar babies like her and it’s just a theme...he just wanted to see what she would do (of course as an additional twist it could turn out his daughter is there to get some spending money and winds up in a dark room orgy with him and our lead).

 

[UsuallyPresent]

Wouldn't even have to be a dark room orgy. Having either of them in a compromising position & see the other approaching would be a hot incestuous hook. Especially if there's no quick escape available. Light bondage, deeply invested fuck partner, even a room with only one door.

 

[Soma99]

Not exactly what the OP wanted but it could go the other way- older guy admits he is having more and more trouble getting hard and isn’t sure he needs a sugar baby anymore.

She tries more and more dirty and kinky things to keep him. I know that’s not how ED works but this isn’t Web MD either.

 

[UsuallyPresent]

Soma, if you invert expectations, you could also invert the sugarbaby's perspective instead of the sugardaddy's. Maybe the gifts and/or funds aren't needed as much and the workload keeps increasing, making it less and less attractive to them. The sugardaddy has to work harder to keep the sugarbaby in the relationship.

You could combine both inversions - aging sugar daddy losing interest and newly financially secure sugar baby - if you wished. Could be a very 'literary' story, neither side of the equation wants to keep going but neither side wants to make a stand, either, so both keep things going along as all the joy leaches away.

 

[Soma99]

Soma, if you invert expectations, you could also invert the sugarbaby's perspective instead of the sugardaddy's. Maybe the gifts and/or funds aren't needed as much and the workload keeps increasing, making it less and less attractive to them. The sugardaddy has to work harder to keep the sugarbaby in the relationship.

You could combine both inversions - aging sugar daddy losing interest and newly financially secure sugar baby - if you wished. Could be a very 'literary' story, neither side of the equation wants to keep going but neither side wants to make a stand, either, so both keep things going along as all the joy leaches away.

That is some dark shit.

 

[UsuallyPresent]

That is some dark shit.

*bow* Thank'ee kindly for your kind words.... *half-hidden grin*

 

[Cliffhere4fun]

Living all these ideas. Hope to read stories about them.