The Pain of Success Part 1

Started by Janine_G, September 26, 2026, 02:58:57 PM

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Janine_G

Lindsey Brooks Success posed with a stern smile, her business suit straining against her big bust as she crossed her arms at the direction of the photographer.  This would be another cover article about her imnpact on the business world.  Having navigated the recovery of yet her third fortune 500 company that had been floundering prior to her recruitment.  She was a star, the business world respected her, and many feared her.  She was smart, cunning and ruthless when necessary.  In fact, her last name said it all--Lindsey knew nothing other than success and was known to not stop at anything other than that. She had been born into a blue collar family and while she kept much of her childhood private, she was known as an accomplished athlete, full scholarship to Stanford and then Wharton for business school.  At the age of 35, she had taken a floundering conglomerate and led it out of near-bankruptcy to dominance in its industry.  She left and within 2 years did the same for a boutique apparel corporation.  She had just successfully turned around one of the largest service coroporations in the world.  She was valued at over 400 million dollars, was known to own at least four residences and several other properties and was considered, at the age of 42 to be one of the most accomplished business people of her generation. 

Her private life was fairly locked down. Security teams kept paparazzi away, even from a distance and she only went to required events either alone, with one of her sisters, or occasionally with a love interest, which was sometimes a man and sometimes a woman. That was one of the only things known about her private life--she was bisexual, and that made her even more engaging to the public, because she was strikingly attractive and both men and women fantasized about her.  She was 5' 9 with full breasts, perfect skin and one very special trait:  she had red hair.  The world loves a redhead.  Especially a sexy, successful redhead.

Lindsey protected her private life for several reasons: 1.  She could and it was no one else's business.
2. She didn't want her private life to get in the way of her work. 3.  She had some interests that she preferred not to share. 

In particular, Lindsey found pain a turn on.  Inflicting it and receiving it, she got excited by it. Lindsey first explored the world of S&M, but found that over time, it wasn't enough, it was too safe and it lacked something--it lacked uncertainty, it lacked competition and challenge, which was her true aphrodesiac.  And then she actually got into a physical altercation with a drunk lover.  She beat the shit out of the other woman, but the fight turned her on so much that she realized that she needed that type of competition.  She fought men, women, she even fought a transexual once who fucked her brains out even though Lindsey had won the fight. 

Alas, not surprisingly, Lindsey always won.  She was a force to be reckoned with, she wanted more.  She thought about finding a professional, or someone physically bigger, but she realized that wasn't what she was looking for--that would be too artificial.  She wanted to find competition that was truly challenging from a perceived equal.

It was October 16, Lindsey remembered it well. She was closing a deal to purchase a company that was struggling and she had met their COO, a stunning man with bright eyes, a square jaw and salt-and-pepper hair.  He didn't like how terse and stern she was and they had exchanged some words during the final negotiations meeting, but in the end came to terms and shook hands.  That evening the air was crisp and it made Lindsey's nipples hard as she stood on the observation deck of the Empire State Building holding an obligatory glass of the evening's "signature cocktail" while she stared downtown at One World Trade.  It was a charity event that she was required to attend.  The only redeeming aspect of the event was that she actually genuinely loved the charity and supported it aggressively because of that, but being in these absurd events with all of the fake people was off-putting for her.  Her cocktail dress almost blew up to reveal her lack of underwear and her bullet vibrator that she often inserted for her own entertainment at these events.  Her breasts strained at the black fabric of her dress, and her red hair billowed in the ever-present breeze at this height in New York City.  She looked at her watch and happily recognized that she had spent enough time at the event.  She texted her driver and turned from the view to leave and almost ran into the COO of the company she had just purchased.  Gregory.  His name was Gregory.

They exchanged pleasantries.  They warmed to one another. She was turned on, and thought she might want to fuck him.  They laughed about their earlier disagreements and chalked it up to business.  She took him home and fucked his brains out.  Like many of her lovers, he couldn't keep up with her, but unlike most, he didn't give in and he had an amazing cock.  It was massive, he was stunning, and she enjoyed the sex, even without the fight. They fucked four times that night, and to her pleasure, he desperately tried to make her climax, but she knew he wouldn't be able to, and warned him of that.  She didn't tell him why.

At first it was casual, and they both saw other people, but she enjoyed his company and they spent more time together.  He was wealthy, certainly not as wealthy as she was, but enough that he wasn't intimidated by hers, and she liked that too.  After a few months and a growing trust between them, she shared the issue.  He smiled at her and said a few simple things that were amazing for her:

"I will never strike you.  I cannot.  I grew up in a house of abuse and will never do that to someone I love.  I will participate in some level of bondage play if you want, but it sounds like that is no longer satisfying for you.  I really like you though, and I have a thought if it works for you.  What if I help find competition for you and then we fuck, or whatever?"

She smiled at his thoughtfulness.  "I've never tried that--usually the person I am fighting is the person I am fucking, but I am open to seeing how that goes.  Would you be open to a threesome if that is where it has to go?"

He laughed, "Lindsey, I don't know an adult male in the world who would turn down his girl's suggestion of a threesome."

And so it was that Greg one day texted Lindsey and said, "I have a surprise, I'll meet you at your apartment tonight at 11 pm."  Lindsey was so turned on she simply left her office.

She was excited about the possibility of how this would go and at 11, Greg showed up with a woman named Kortney.  He didn't explain how he had found her, but she was very attractive, and understand why she was there.  She went into one of the rooms and changed, as instructed.  Lindsey had asked her about fighting naked, as it allowed her more pain and the woman only asked for one rule:  her face needed to stay unblemished.  Lindsey appreciated that and agreed immediately.

The two women walked out into the room Lindsey had set up for this, Kortney in red and Lindsey in blue, dropped their robes and charged at each other.  Kortney got a hold of Lindsey's hair and threw her to the ground.  Lindsey was pleased, the other woman was strong and aggressive.  As she scrambled to her feet.  Kortney threw punches at her body and took blows from Lindsey.  The brunette grabbed Lindsey's vagina and dug her nails in.  The pain set off triggers in Lindsey's body and the redhead felt an incredible rush of pleasure.  She battered Kortney and Kortney punished her.  It was a good fight, but Kortney quickly began to lose ground and then ultimately was battered into submission by Lindsey.  Lindsey was turned on and Kortney left with a polite good night as Lindsey and Greg never made it to the bedroom.  The sex was amazing, but the fight was not enough of a challenge for Lindsey to get her to the point of climax.

Greg laughed afterwards as they sat in post-coital bliss, Lindsey's body scratched and bruised.

"Well, I have to say it was a huge turn on for me to see the two of you fight. I can do this any day. "

She laughed.  "You are the first person who has ever tried to do something like this for me.  It's amazing.  Find someone tougher and we're getting closer..."

"Noted. I will work harder to find the next participant..."

She smiled, and mounted him again.

To be continued.