It is from Rin x Sen + Ran->Sem: Cross Mix.
Both episodes can be watched from here:
https://hentaimama.io/tvshows/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen/
The GIF happens in Episode 1 at 09:58 mark
https://hentaimama.io/episodes/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen-episode-1/
Both episodes can be watched from here:
https://hentaimama.io/tvshows/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen/
The GIF happens in Episode 1 at 09:58 mark
https://hentaimama.io/episodes/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen-episode-1/
Terra, jetokep226, fatrat1 and fangamesxxx confirms this as correct.
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It is from Rin x Sen + Ran->Sem: Cross Mix.
Both episodes can be watched from here:
https://hentaimama.io/tvshows/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen/
The GIF happens in Episode 1 at 09:58 mark
https://hentaimama.io/episodes/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen-episode-1/
Both episodes can be watched from here:
https://hentaimama.io/tvshows/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen/
The GIF happens in Episode 1 at 09:58 mark
https://hentaimama.io/episodes/rin-x-sen-ran-sem-cross-mix-haru-urara-uragiri-to-zetsubou-no-kisetsu-hen-episode-1/
Terra, jetokep226, fatrat1 and fangamesxxx confirms this as correct.
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