Boss Needs a Date

[RoleplayLiterate]

I've been wanting to do a sort of tried and true troupe of the boss needing a date for some event and asking one of his employees to take his wife and of course they end up having sex.

But I'm need maybe a fresh idea or twist for it. Anyone wanna brainstorm a little. Tell me your thoughts about this sort of scenario, what you like and don't? What you wish you could see?

For me personally I'm not into humiliation in a big degree so I don't wanna go that route. But I'm open to thoughts and ideas.

Let's inspire each other.

 

[OnlyHappyEndings]

Ambitious employees and their wives compete for the boss's attention, hopeful it will further their careers. The boss is a brilliant business man but kind of clueless about interpersonal relationships.

Dick's wife Jane seems to have the formula for success since the boss frequently taps her for social duties. After each event she proudly comes home and fills her husband in on the details.

Dick loves hearing about her dates, mainly because of the career boost he is expecting but also because of what a hot piece of ass Jane is. She'll start off talking about the event itself and the process of seduction but he secretly just wants her to get to the good part.

It occurs to Dick that Jane might end up with the boss permanently. In that case his goose is cooked, because who wants the ex hanging around? He guesses he'll just have to trust her.

 

[taimur40]

Not sure if this can help, but here it is.

1. Alex was doing a job as a VP in a company, but he wanted to start his own company (startup). Alex had a product idea, but lack investment.

2. Alex found a cofounder, Jack and together they develop a prototype.

3. Alex hired Emmy as the first employee. For Emmy, it was her job after a long break, so she was willing to join a startup to get going.

4. They were connected to an investment firm and was asked for a presentation. At the last moment, Alex come to know that Jack was convicted in the past. He knew that the investor(s) would certainly do the background check before putting any money into their business and this will screw up everything. The investors are all well connected in general, so this will keep on coming after him in future.

5. At the last moment, Alex removed Jack name from the presentation and put Emmy instead.

6. Alex & Emmy flew for the presentation to secure pre-seed funding from the investors.

7. In the investors office, they come to know that they are not the only startup, pitching their idea and the investors usually pick only top 2 or 3 at max in one batch. They had the last turn, so Alex was a little nervous. Up till now, he was funding the startup from his own savings and he needed to have the investment soon before burning out his funds.

8. When they enter the board room, they found 2 female directors and 1 male director of the firm.

9. Investors like the product, but told them that the other participants products are also considerable and its kind of a tie. In this scenario, the firm policy is to prefer the company having the women ownership in the company.

10. Alex spontaneously said on the spot that .... its their lucky day in this case, as Emmy owns his startup equally being his wife, which was a surprise for Emmy, but she played the part.

11. During the negotiations, another guy step in the board room (say Greg), who was Associate Financial Controller of the firm and he had to fill in because the CFO (Chief Financial Officer) had to leave due to an emergency. Greg happened to be ex boyfriend of Emmy few years back.

 

[taimur40]

12. After exiting the room, for some strange reasons, Alex felt that they would not get the investment, perhaps he didn't perform well. He apologize Emmy for putting her on spot. Emmy jokingly said ... if they get the investment, he'll loose 50% of his equity because of the stunt he pulled, to which Alex bantered ... No, I won't, in that case, you'll be my wife.

13. Alex suggested to buy lunch and while in the cafeteria (during lunch), Greg showed up. He congratulated Emmy for her wedding and told them to hang around, as they have good chance for getting the investment.

14. They were invited for the company dinner, as couple, with news of successful investment in their startup.

 

[Rob_Royale]

Hmm. Older employee, say 60, in a new start-up run by a 28 year old. The employee has had a rough career. Every time there's a dip in the economy he's frequently laid off. He's rather desperate to keep this job until he can retire. So when his boss admits to needing a plus one for a future engagement, while at a company party, he's quick to suggest his 48 year old wife. Both are on their second marriage and things are kind of loose. Not quite an open marriage. Loose. He knows his wife has a little crush on his young boss and figures no matter what happens it can only help him.

His wife is at the party and is just stunning. She smiles at the suggestion. "I'd love to go with you, if you wouldn't mind having an old lady on your arm?"

The young man is star struck in front of this gorgeous MILF. "I'd like that very much. "

She gives him a seductive smile that promises so much that he can't help but shudder in arousal.

 

[RoleplayLiterate]

Hmm. Older employee, say 60, in a new start-up run by a 28 year old. The employee has had a rough career. Every time there's a dip in the economy he's frequently laid off. He's rather desperate to keep this job until he can retire. So when his boss admits to needing a plus one for a future engagement, while at a company party, he's quick to suggest his 48 year old wife. Both are on their second marriage and things are kind of loose. Not quite an open marriage. Loose. He knows his wife has a little crush on his young boss and figures no matter what happens it can only help him.

His wife is at the party and is just stunning. She smiles at the suggestion. "I'd love to go with you, if you wouldn't mind having an old lady on your arm?"

The young man is star struck in front of this gorgeous MILF. "I'd like that very much. "

She gives him a seductive smile that promises so much that he can't help but shudder in arousal.

Really really like this idea. Gonna mull it over some more!

 

[PennyThompson]

Rob's idea is pretty dang hot

What about other combinations besides male boss and male employee's wife? Or what if it doesn't START as a date?

What if the boss (older male) needs to host a business dinner with a client... The client is a rich conservative woman, kind of eccentric, and she doesn't feel comfortable doing a one-on-one with a male stranger. So the boss asks the only woman available on short notice to join him at the dinner, his young female executive assistant.

They get to the restaurant and before the boss can make proper introductions, the client starts gushing, "oh what a beautiful daughter you have! I just love when businesses are a family affair, this really reflects well on you..." Etc, so they decide to play along with it to ensure the deal goes through.

Extend the farce, maybe the rich client insists that boss and "daughter," join her on her yacht for the weekend as they negotiate the deal, it's too big to pass up. "There's only one guest cabin, but you're family, I'm sure you won't mind."

Add some accidental sexy hijinks, some continued mistaken identity, really go all in on the taboo-but-not-really aspect of it!

 

[RoleplayLiterate]

Rob's idea is pretty dang hot

What about other combinations besides male boss and male employee's wife? Or what if it doesn't START as a date?

What if the boss (older male) needs to host a business dinner with a client... The client is a rich conservative woman, kind of eccentric, and she doesn't feel comfortable doing a one-on-one with a male stranger. So the boss asks the only woman available on short notice to join him at the dinner, his young female executive assistant.

They get to the restaurant and before the boss can make proper introductions, the client starts gushing, "oh what a beautiful daughter you have! I just love when businesses are a family affair, this really reflects well on you..." Etc, so they decide to play along with it to ensure the deal goes through.

Extend the farce, maybe the rich client insists that boss and "daughter," join her on her yacht for the weekend as they negotiate the deal, it's too big to pass up. "There's only one guest cabin, but you're family, I'm sure you won't mind."

Add some accidental sexy hijinks, some continued mistaken identity, really go all in on the taboo-but-not-really aspect of it!

Another very good idea. Definitely worth exploring. Though incest (even faked) is hard to monitize on Patreon or elsewhere. Though obviously doesn't have to be. But I like keeping my options open.

 

[jaF0]

What about other combinations besides male boss and male employee's wife?

Female boss with mostly female staff. She wants one of their Husbands to accompany her.


Staffers get competitive at offering their Hubbies, hoping some favoritism will follow when it comes to raises and promotions.

 

[Reshbod]

Hmm. Older employee, say 60, in a new start-up run by a 28 year old. The employee has had a rough career. Every time there's a dip in the economy he's frequently laid off. He's rather desperate to keep this job until he can retire. So when his boss admits to needing a plus one for a future engagement, while at a company party, he's quick to suggest his 48 year old wife. Both are on their second marriage and things are kind of loose. Not quite an open marriage. Loose. He knows his wife has a little crush on his young boss and figures no matter what happens it can only help him.

His wife is at the party and is just stunning. She smiles at the suggestion. "I'd love to go with you, if you wouldn't mind having an old lady on your arm?"

The young man is star struck in front of this gorgeous MILF. "I'd like that very much. "

She gives him a seductive smile that promises so much that he can't help but shudder in arousal.

I had a similar idea to this and would love to see it written. I'd make her a little older, say 55 and they not be in an open or similar type relationship. I think she agrees to be his arm candy for the night and is charmed by him and agrees to go further and further over the course of the "date". He has a hot milf and she feels appreciated by the younger man.

 

[RoleplayLiterate]

I had a similar idea to this and would love to see it written. I'd make her a little older, say 55 and they not be in an open or similar type relationship. I think she agrees to be his arm candy for the night and is charmed by him and agrees to go further and further over the course of the "date". He has a hot milf and she feels appreciated by the younger man.

Now here's a question. I keep seeing people say they are open, which is fine. Totally cool playing that card. But what if they were just mature trusting and understanding and though they don't have permission they "cheat" but come clean all about it and are understanding that it was just sex, not an actual affair because of lack of intimacy. That may be a bit more complex but I kinda like exploring dynamics beyond "oh they are open so it's cool"

 

[Soma99]

Female boss who ends up having sex with her female employees husband. The boss is drunk and wants some kind of embarrassing kink- maybe not kink but like just an odd kinda thing- like she can only cum if she’s being called winne the poo


Ok maybe the guy has a curved dick or something that makes the boss cum harder than ever

Whatever

The employee is fine with it- but she does enjoy teasing the boss at work now- not humiliating but teasing…. But now that the boss knows there is a possibility it could happen again she really wants it to… now negotiating starts, or suddenly there are all these events she needs a date for

 

[jaF0]

Female boss with mostly female staff. She wants one of their Husbands to accompany her.


Staffers get competitive at offering their Hubbies, hoping some favoritism will follow when it comes to raises and promotions.

Candace Bergen played Murphy Brown from age 42 to age 52. That would be a perfect role model for this character. Brash, bold and not at all unappealing.