Work Header

Who Can Screw the Shepherd Siblings Better? A Sex Bet Between Addison Montgomery and Mark Sloan.

Chapter Text


Who can Screw the Shepherd Siblings Better? 

A Sex Bet Between Addison Montgomery and Mark Sloan.


Who can Screw all of the shepherd siblings better? Addison Montgomery or Mark Sloan? And what happens when Addison ups the ante and adds the Grey sisters into the mix? Rated M.





Chapter 1: The Beginning.





Mark Sloan was Addison Montgomery’s very first kiss when they were four.


It was not Derek, but Mark she had pulled under the playset and cradled their lips together.


Addison kissed Derek next they were six. 


But she never told him that he was second for her before they were married.


Before they were married (Derek and Addison, that is).


Addison and Mark had a sex bet going on.


Who could screw all the Shepherd siblings first?


Who could screw them the most? 


And last but not least most importantly,


Who could screw them better than whom,


But without telling Derek or any of his sisters what was really going on between them.


When Mark took on this bet, he never realized he even had the potential to lose. 


Mark Sloan thought that Addison wouldn’t get very far at all.


Because women weren’t really her thing, now were they?


And that women weren’t even a Nancy or a Liz or a Kathleen or Amelia’s thing either.


So that in the beginning, Mark Sloan thought that he stood a fair chance of winning. 


And even on the off chance that he lost, that he still had something else to gain.


Thinking that if Addison won maybe she’d screw him again after. 


And that she’d leave Derek for Mark and they both could live happily ever after together.


When Mark took on this bet, he never realized the one reason he had the potential to lose. 


Which was that Addison had already screwed Derek and married him.


And that most of all, that Mark wasn’t about to get in bed with a boy. 


Even to win this stupid bet over Addison.


And Addison on the other hand.


Was just waiting to prove Mark Sloan wrong in any way she had. 


Including becoming a lesbian.


And flipping the Shepherd sisters into the same. 








Chapter Text


Chapter 2: The Middle.



Addison made her first move the very next day. 


She asks Kathleen Shepherd for help with her homework.


And then she took her in the back of her car.


She was seventeen years old in the back of her Mercedes. 


And wow, was Addison hooked. 


Mark took Kathleen next, in the backroom at college.


He hid her away from the professors and from all the students’ stares. 


And then Addison took Nancy next,


New years after she’d given her food poisoning that November.


Addison said that she’d owed her. To make her feel good for a change. 


And Mark had Nancy over next, in the back of HIS car. 


And Nancy never went back to men at all after that. 


And Addison had Liz bent over backward on the kitchen counter.


Because Liz was after begging her for it.


After she kisses her neck wantonly. 


And Mark took Liz on Addison’s bed.


Because he was so mad that she’d gotten to her first.


And that when he finally made her come,


That he could see wisps of Addison’s red hair fall off of her shirt.  


And then Addison saved Amelia for her very, very last. 


Because Amelia was the baby of the family.


And so she waited until they were both in med school.


And Amelia was the one to finally ask Addison.


Because she’d always wanted to be with a woman before. 


And Addison agreed it was worth it. 


And Amelia Shepherd was the first woman ever,


That Addison had ever made to scream out her name. 


And then Addison and Derek got Married. 


And Derek stopped ever coming home.


And then Addison was lonely.


And Mark Sloan was there.


And so they said they’d kissed each other once.


And it would be their little secret.


No one had to know that they did it. 


And no one had to find out about their sex bet still.


Except then Derek did come home.


To kick Mark Sloan out of his house.


And left Addison in the rain.


Before letting her back in as he left her.


As he walked away, set for Seattle.


And she never followed him.


For months she stayed with Mark.


Until she aborted his baby.


And never told him she did. 


And Addison didn’t want to talk to Mark at all anymore.

And she didn’t want to tell him why.


So she went in search of Seattle. 


To see what Derek had been up to.


And this was the start of a whole other story. 













Chapter Text


Chapter 3: The Ending.



And then Addison showed up later.


To see her husband screwing Meredith Grey. 


And so Addison finally called Mark again. To talk about the sex bet.


And they never actually settled their bet, YET. Because Mark had stopped keeping score.


After Addison had moved to Seattle, he had thought that all of it was already over. 


He said that he was being a gentleman, that he would let her surrender gracefully.


That there’s no way that Addie could win over him from a thousand of miles away.


But that’s just when Addison upped him the ante, adding a new family into play.


Adding also the “who could bed THE Meredith Grey and both her sisters, Lexie and Molly.”


Because she figured if they fucked with that family enough, they could make Derek leave her.


He’d leave Meredith for once and for all.


So that Addison would have already one with more points than him. 


And then Addison could finally have some peace and her husband back.


And Mark came to Seattle at Addison’s beck and call. 


Falling into bed with Addison first on the night of her divorce.


He said she could back out if she wanted to. 


But now she said she wanted to finish it even more.


So Mark hit on Meredith first when he walked into the hospital. 


And it landed him with a black eye and a fall to his face.


Mark tried with Molly Grey when she showed up there again.


But she had a hot soldier husband and a baby and she didn’t want anything to do with him.


Addison, by contrast, was begged to by Molly when she was at work. 


Molly was reacting to the painkillers during her second pregnancy.


She was needing some tender touches just to get her through the rough labor. 


And Molly called her hot soldier husband in front of her and Addison, and he said it was okay. 


And so Addison fastened her lips to the space between the woman’s open thighs. 


And she licked and she sucked and she licked and he sucked until she was licking some more.


Until Molly stopped screaming in pain and started screaming for joy all into her instead.


And when Lexie showed up all the way in from Harvard, the only person she wanted to talk to,


Was her long-estranged sister Doctor Meredith Grey. And little did LittleGrey know at the time,


Mark had an on ending crush on her and didn’t want to mess around with a twenty-four-year-old.


And Lexie was hurting because Meredith hated her. 


And Lexie was annoyed when Mark started hitting on her. 


So she fell into Addison’s comforting arms and let her kiss goodnight and to soothe her to sleep. 


And when Addison woke up the next morning she was about to be fucked by Lexie Grey.


Mark screwed Lexie eventually, but he never got to Meredith, even when Derek was with Rose.


Meredith and Derek were soon to be married after Mark helped and he finally proposed again.  


And Mark started counting up his points in his head to see how far he had to go to still win.


And Addison also started counting up HER points to see how far he had to go to still win.


And Mark took Amelia later after Derek got shot. 


Because she said he could call her hot. 


And he did then he screwed her hard. 


And after this happened.


Mark was still single and alone. 


Until he started seeing Lexie in Secret. 


Until Derek found out and he was on the ground again.


And Meredith led him away by the hand.


And Lexie led Mark out by the hand.


And Alex Karev told Addison he was "her guy, now"


And that was the only time,


That Addison didn't regret kissing Alexx. 


And so Addison was all alone then.


She thought she would leave for LA but she never left.


And years and years later, they all still were friends.


Addison, Derek, Meredith and Mark.


While Derek was going to marry Meredith.


And Mark was going steady with Lexie. 


And Addison was still the only one who was all alone.


And when Meredith thought that her child was going to be taken away from her, 


She didn’t want comfort from Derek who would only blame her and make her upset.


Instead, she went looking for Addison, who had every reason to hate her yet still cared for her.


And she asked Addison how Derek could possibly have left someone so perfect as her. 


And Addison said that it was because Meredith was better, better than she was.


That Addison had always admired that Meredith was more perfect in all ways compared to her.


And then Meredith just wanted to comfort HER. And take away some of the pain.


She thought she had caused it all. And when Addison told her it wasn’t really her fault,


Meredith stifled her excuses and stories and explanations with rushed kisses and groans. 


And when Addison finally comes clean about the bet, all Meredith does is break out in a grin. 


And Meredith said to her after all of that pain stopped.


That she REALLY that she hoped that Addison would win.


Especially if SHE also got to screw Amelia Shepherd and still date Addison.


And Addison agreed. And Meredith said she would do anything for Addison. 


And that she would offer up anything she had to help her beat out Mark Sloan. 


And when Derek walked in on his fiancé screwing his ex-wife into submission in his bed,


He left the papers for Zola’s adoption for her filled out with only Meredith’s name on them.


He left both the wedding ring he had for her and his own on the table as he left her.


And Derek walked out alone to his trailer to drink scotch and to cry.


And then Derek called the only person he ever truly loved. 


And that was his childhood very best friend named Mark Sloan. 


And Sloan told him that he screwed all his sisters and that Addison had as well. 


And he told him that Meredith and Lexie and Molly were a part of the plan. 


But that he never got into any of their pants and yet Addison already did. 


And then Derek says he wants Mark to try to even beat her out any more. 


Addison having ruined not only her marriage with him. 


But also his engagement with Meredith.


And when Derek finally laughed about the absurdity of it all, 


Derek crawled into Mark's arms


And then Mark waited for a long time. 


As Derek cried in his care.


When Mark finally said to him:


You know we’re not finished yet. There’s one thing I haven’t tried. One more point we could win.


Just to feel like we both have lost out by a little less. 


Mark says he’s had all the Shepherd’s sisters, yet none of the Grey’s.


But there’s one Shepherd sibling I still haven’t ever asked out yet. 


And all these years, I’ve been saving the very best Shepherd of all to be my last.


And when Derek finally kisses him back. 


That’s when he knows that no matter who or what Addison has done. 


That he feels that he and Derek have finally won. 


Even though, in all technicality,


Which they all discussed later,


Mark, Derek, Meredith, and Addison,


That the final win went to Addie.


And Meredith proposed to Addison on the spot.


And Addison said yes to her.


And Derek cried saying his ex-girlfriend left him for his ex-wife.


And Mark said he would marry Derek.


And Derek said yes to him.


And when they plan to have a double wedding, 


All of the shepherd and grey sisters mingle around awkwardly at the bachelor party.


Telling stories about how Addison and Mark had both been with them in bed or not.


And Mark has to talk Derek out of punching Meredith grey right square in the face.


Because she gave her wedding ring to his ex-wife to propose to his ex-girlfriend.


All these years Addison had thought Mrs. Carolyn. Shepherd hated her.


But it turned out she just wanted better for both her and Derek. 


And that she knew that for each that their one true love,


Would come to find them someday. 


The one that Addison had one.


And had gotten a prize for at the wedding. 


Which was Mark saying he was sorry,


That he thought she would lose. 


And so they're all happily married.


And they don't talk about the bet.


Until one day doctor, Margaret Pierce shows up at Grey-Sloan Memorial.


Looking to find her long-lost sister Doctor Meredith Grey. 


And Addison Montgomery and Mark Sloan start their betting all over again.


And Meredith says to Addison she should go for the win. 


And Addison does. 


And she finally does win again.


And they all lived happily ever after that.



Or at the very least, that’s a wager that we could all very well hedge our bets on.













***** FIN.