Let the threesomes begin!

With 9 ladies, this is complicated.
They make it work, as they split up into 4 groups of 2.

Salma stays out, since she only does sexual stuff with Jack and Catherine (barring some exceptions).

Teyonnah and Brittany.
Megan and Jennifer.
Lana and Jessica.
Gabrielle and Serena.

Jack hooks up with Gabrielle and Serena first.
Both ladies are new to him after all.

Ms. Williams lays back on the big pool chair.
Ms. Union is on top of her.

The pair kiss and spread their legs for Jack.
He fucks Serena first.

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Brent is hooking up with the duo of Teyonnah and Brittany.

They are side by side on smaller pool chairs.
They are in doggy position as he decides who to fuck first.

He chooses the 'Pitch Perfect' Actress first.

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Jack enjoys Serena, remembering when he saw nearly all of her in a Photo Shoot...

He makes her cum.

As he switches to the TV Star, Serena asserts her dominance by grabbing Gabrielle's arms and holding them behind her back.

She has to just lay there and take his cock, as her pussy sometimes rubs on the Tennis Player's torso to boot.
She kisses her all over her neck too, teasing her with a mouth-to-mouth kiss.