Context: After a blind date with a tomboy, you find out that she is a CEO.

Tags: [F4M] [Wholesome] [Comfort] [Spicy] [Reverse comfort]

Usage: You may tweak or record this script.

Monetization: All forms of monetization are OK with me! YouTube, Patreon, etc. I would appreciate being able to listen to the recording, if possible. Let me know if you have any questions. Thank you!

[Scene opens up with you walking into the mansion of your GF]

***

[SFX: Boots walking]

“Ugh. I am so done right now.”

[She takes off her jacket and lands on the couch]

“All of this. This after dealing with those board members I feel exhausted.”

[SFX: waling on marble]

“To make matters worse, I have to go to another meeting in a few days. I just need a little time to myself that’s all. Is that really too much to ask for, Winston?”

[He shakes his head]

“Say Winston, remember that very sweet, handsome, and young man that I was talking to earlier?”

[Pause]

“Is there any possibility that you can bring him here~?”

[He asks if you know him?]

“Oh, I know him alright. You see we met at a blind date. Set up from one of my… Friends.”

[Pause]

“They were so nice to me when we first met. We started talking about different things.”

[Winston asks for examples]

“Well for starters, we talked a little bit about the sports standing. Nothing too boring. Mostly about… Draft leagues. We also discussed certain players that we thought were going to do well this season.”

[He asks where could he find him?]

“that’s the thing Winston. The only thing he gave me was the address of his work.”

[SFX: Shuffling paper]

“He says that he didn’t really want to see where he lives. He was probably too shy or embarrassed to show where he lives. Either way, I can respect someone who wishes to keep their privacy.”

[Winston nods and walks away]

“Ah~. To see his loving face again, maybe that would help me feel better. I wonder if he knows, if I’m a CEO.”

[She starts to worry]

“Or even worse, he doesn’t like the idea of a woman being this successful. No, no, no. There’s no way. I mean, the two of us were getting along greatly.”

[She still worries]

“Although maybe I should get into something a little more… Comfortable.”

[SFX: Shuffling through cloths]

“There the same outfit that he saw me in our first date.”

[SFX: Brushing cloths and smelling]

“I’m actually surprised that Winston actually washed all of this. Must have taken them quite some time to get all those stains off. I think it’ll be a while before I go to a sports bar for a date.”

[She chuckles a little]

“Hard to believe that I spilled all of that Nacho cheese on my favorite jersey.”

[Some time goes by.]

[SFX: Phone vibrating]

“Oh Winston. Did you find the man I was looking for?”

[Winston says yes]

“Excellent! Be sure to give him the special treatment Winston. And above all else, don’t scare him.”

[He agrees and hangs up the phone.]

“Oh, I can’t wait to see him again.”

[SFX: Car pulling up]

“Oh, that must be them.”

[SFX: Door opening up]

“Thank you for bringing him here today Winston. Since you were so kind to me today is there anything you wish within my power Winston?”

[He asks for a treat from the sweet cabinet]

“Ah. The sweet cabinet. That’s fair. Be sure not to spoil your appetite though.”

[You step out and are greeted by a beautiful tomboy]

“it’s good to see you again. Did Winston treat you well?”

[You nod]

“That’s great. He often gives the impression of a hit-man. Deep down though; He’s a big softie.”

[You ask if this is a friend’s house]

“A friends house? Oh, that’s right. I never did invite you over to my place.”

[She gets closer to you]

“No, my dear. This is my house.”

[You a little shocked]

“I hope this doesn’t bother you my dear.”

[You shake your head]

“Good. Because the last man I was with, found it rather… Intimidating being in front of a large building. Only to find out that it is indeed my house. Or as many often people call it their home.”

[You ask why she doesn’t call it a home]

“Well, the reason I don’t call it a home is because a home is where your family is. Currently I have none.”

[You look at her sadly]

“Hey, no worries. These things happen.”

[Pause]

“I bet there is some questions that you have about what I do.”

[You nod]

“Well, to put it simply. I’m currently the CEO of my own company.”

[Pause]

"Is there a problem?"

[You ask how was she able to just mingle while being CEO]

"How am I able to mingle? I mean, that is a fair question. Most CEO's tend to be practically living in their businesses. Well, since starting my company; I tend to have a bit of a...hands off approach. At least in the board room."

[You raise an eyebrow]

"Now don't get me wrong. When it comes to big issues and buyouts, I'm always there. The company however, is practically "Self-run" that all we need to do at times is just check in here and there."

[You ask what her business is]

"*Giggle* Well, considering we met at a sports bar; isn't it obvious?"

[Your shocked]

"That's right. I am the one who created that sports bar chain. It was initially an idea my dad had all those years ago. Fortunately for him, his only child; that being me, was a massive tomboy who loved sports."

[Pause]

"The downside however is that most guys I tried getting into relationships with were either in three kind of categories."

[Pause]

"The first just consider me a friend. Nothing wrong with it. It's just...you know, kind of a bummer. The second find it intimidating that I'm a very successful businesswoman. Finally there's the third...ugh! these guys."

[You ask what's wrong]

"I mean, I don't mind spoiling my dates...arguably too much in some cases. It's just some of them take it way too far. I mean, I hadn't thought of being a "Sugar Mommy" it's just some thing's I don't mind them helping with."

[Pause]

"For example, let's say we decide to do something together where we both might benefit. Say for instance, an opening of a new sports bar. We both can have fun and enjoy all the fruits of our labor. These guys however, just want to be spoiled."

[Pause]

"I just don't know sometimes."

[You explain that you would consider being a boyfriend on one condition]

"Oh~? Thinking of filling in the BF role? Ok, what's your condition?"

[You explain the condition]

"You...you want to spoil me just as much as I spoil you? How do you plan on doing that?"

[Pause]

"I see, I guess that could work. Ok, I'll let you have a go at being my BF. Also, if it doesn't work; would you be cool in being just friends?"

[Pause]

"Truth be told, it's been a while since I seen someone as cool as you."

[You nod]

"Great, then let me give you the tour of the house."

[You two walk into the mansion as it fades to black]

[To be continued...?]

Note: Still some kinks to work out, I'll try to iron them out in part 2. Hope you all have a lovely day/night.