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May was the fifth month of 2016. The month started out rather uneventfully, although it did see Chris getting a new body pillow as a substitute for a sweetheart. Things picked up towards the latter half of the month, when Chris revealed that he was competing with a former gay porn star for the privilege of supposedly impregnating a lesbian couple. The two competitors released sex tapes for viewers to vote on, reminiscent of the Liquid Chris saga.
- 7 May - Chris's Etsy shop closes temporarily.
- 10 May - Chris buys a dakimakura (anime love pillow).
- 14 May - Chris announces plans for Sega to claim partial ownership of the Sonichu brand.
- 15 May - Chris files a petition to change his name from Christian to Christine.
- 15 May - Chris posts on Facebook about eating McDonald's pancakes.
- 16 May - Chris reiterates his support for transgender bathrooms on Facebook.
- 18 May - Chris offers parenting suggestions on Facebook.
- 23 May - Chris makes a short video in which he begs for donations again and introduces his new waifu Naru.
- 23 May - Chris uploads a stream of himself playing Uncharted with Naru at his side.
- 25 May - The donations request on his Etsy account is removed. He adds a support button to his YouTube account.
- 26 May - Chris posts another livestream video in which he completes an Uncharted level.
- 26 May - Chris repeats his request that people give him money through YouTube.
- 28 May - Over a loud techno beat, Chris relates in a video how he is being bullied by a troll named Johan.
- 31 May - Chris uploads a video of him humping a sex doll. He has clearly not learned anything from the first time he tried this.
- 31 May - In a short video, Chris asks viewers to vote for his doll-humping video and not Johan's.