olivia would Archives

March 27, 2025

Boss Bitch Training

Olivia Would is a boss of a high powered media company who fashions herself on Miranda Priestly, the Meryl Streep character from ‘The Devil Wears Prada’. She is firm, incomparable and won’t take no for a answer, working her staff into overtime to make sure the company excels. When subordinate Naomi Stark, not only messes up her work, but doesn’t seem to take her admonishments seriously, Olivia is not happy and wants to show her what commitment to her job really mean. A rare trans with cis-girl scene on this site, and we’re interested in hearing your feedback. Olivia is an awesome performer, and has the looks and the equipment to dominate, and really gives Naomi a stern seeing to.

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February 6, 2024

Olivia Would Is Up In Your Face!

Today you’re meeting the aptly named Olivia Would, this sexy tall girl certainly has enough wood for you! This sexpot is going to strip for you, show off her sexy feet and let you get up and close with her massive cock as she puts on a hot solo show for your viewing pleasure!

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November 11, 2023

The Complete Package

Olivia Would really is the complete package. She’s a visual feast for the eyes. A smorgasbord of sexuality. She has it all. It’s not just her beautiful features and face, it’s more than that, there is sex appeal in the bucket loads, the way she looks at you as if she’s going to tear you up. Her body is pretty fucking awesome. Breasts are perfect for her body frame, and lovely pink nipples, her skin is smooth and pristine, her cock is frankly ridiculous in its size, width and ability to stay rock hard. Some girls have the IT factor. Olivia Would IS the IT factor.