To unlock this achievement you must watch a racy/sexy video from Gandhara.
This is a guide from psnprofiles that has all the information on how to unlock all the videos. Here's a link to the guide. https://psnprofiles.com/guide/5654-yakuza-0-trophy-guide
Side note: If achievements aren't popping turn your Xbox power option to energy saving instead of instant on.
At Gandhara, you're able to watch videos of the different AV idols. There are 30 of them in total, but various requirements will need to be met in order to unlock them. You'll gain the majority of them simply by completing substories and maxing your friendship gauge with people, but others require you to things which are a little less obvious. While you only need to watch one video to earn this trophy, you need to watch all of them for a Completion Point. Check the table below for information on how to unlock the videos.
Video How to Obtain
Chika Arimura: Complete "A Moment Shared" (Substory #70)
Mana Sakura: Complete "Of Love and Ramen" (Substory #71)
Ai Uehara: Complete "The First Friend" (Substory #72)
Hibiki Otsuki: Complete "A Little Brotherly Love" (Substory #73)
Saki Hatsumi: Complete "Dream Chaser" (Substory #74)
Haruki Sato: Complete "The Flirty Hook-up" (Substory #33)
Ayaka Tomoda: Complete "The Sexy Hook-up" (Substory #32)
Riku Minato: Complete "The Innocent Hook-up" (Substory #31)
Marina Shiraishi: Complete the Real Estate Royale storyline
Kotomi Asakura: Complete the Cabaret Club Czar storyline
Riona Minami: Complete "The Girl in the Video" (Substory #24)
Kokoa Aisu: Complete "Be My Boyfriend!" (Substory #52)
Ayu Sakurai: Complete "How to Train Your Dominatrix" (Substory #7)
Nozomi Hazuki: By maxing out the Komian Chef's friendship gauge
Erika Kitagawa: To obtain this video, you must finish a game of the 'Golden Ball' variant of Pool at the Vincent bar in Kamurocho. This variant is unlocked by finishing three standard games. It doesn't matter if you win or lose, just make sure you quit after each one.
Luka Kanae: By maxing out Luka's friendship gauge
Kyoko Maki: By maxing out Kyoko's friendship gauge
Emiri Okazaki: By maxing out Emiri's friendship gauge
Reika Aiba: Complete "Sugar Daddy" (Substory #10)
Iori Kagawa: Complete "Toilet Talk" (Substory #64)
Ai Haneda: Finish x3 SHINE, Heartbreak Mermaid, or Rouge of Love at Utahime Karaoke Bar in Sotenbori.
Nao Mizuki: Complete "A Watery Investment" (Substory #22)
Yuki Natsume: Order every drink at Maharaja Sotenbori and it should be unlocked the next time you visit Gandhara.
Rina Ito: Complete "How to Train Your Dominatrix" (Substory #7)
Maika: Order every drink at Maharaja Kamurocho and it should be unlocked the next time you visit Gandhara.
Shizuku Hasegawa: Complete "Crossed Words" (Substory #57)
Nanase Otoha: By maxing out Officer Kikuchi's friendship gauge
Riri Kuribayashi: Complete "From The Heart" (Substory #49)
Miku Abeno: Finish x3 SHINE, Heartbreak Mermaid, or Rouge of Love at the Heroine Karaoke Bar in Kamurocho.
Miho Tono: By maxing out Miho's friendship gauge