June 2016 began with Chris’s sex-off competition with Johan coming to a close, with Johan emerging as the victor. Chris was banned from selling on Etsy, due to his failure to send orders. He made a video lying that the account was "on vacation." He ramped up his e-begging campaign, claiming that the money would be used for necessities, such as medication and bills. He also decided to revive his career as an escort, offering to fuck non-transgender women for extremely high prices, giving his hooker name as "Stephanie Bustcakes." Chris resurrected his search to find a caretaker for Barb, once again harassing Cole Smithey on Twitter and Facebook in the belief that insulting someone would make that person want to help you.
- 4 June - Chris uploads two videos of himself with his cat Pollo.
- 5 June - Chris deletes his poll pitting himself against Johan the Bully due to Johan winning.
- 7 June - Chris tells Facebook he has been in "meditative state" lately.
- 11 June - Chris records a video congratulating fan Jonathan for his birthday.
- 11 June - Chris makes a video claiming that his Etsy shop is on vacation, even though it had actually been banned. He says he will move to Zazzle.
- 12 June - Chris reminds his Facebook fans that they can make donations through the support button on his account.
- 13 June - On Facebook, Chris rambles about Transformers and his financial troubles.
- 14 June - Chris makes two [Donations Requested, Please[videos]] pleading for donations to pay for Barbara's asthma meds. Barb herself appears in both, and does not look at all well.
- 17 June - Chris makes a 20-minute video in which he reads the first chapter of a story. Yet again, he begs for money.
- 19 June - Chris posts another dull story-reading video. He begs for donations in a room literally filled with toys he could sell.
- 19 June - On Facebook, Chris remembers his late father Bob on Father's Day.
- 22 June - Chris emerges in a leaked video as "Stephanie Bustcakes," prostituting himself. He won't do anal.
- 26 June - Chris makes a random Facebook comment about hosiery and stockings.
- 26 June - Chris makes an angry Facebook diatribe against his half brother Cole for not providing financial help to him and his mother. He includes a drawing of Cole literally burning money.
- 26 June - Chris makes a rare tweet, directed against Cole for being greedy.
- 29 June - Chris posts a video apologizing to all males while reading off a script.
- 29 June - Chris makes an important video announcement that his autism has been cured thanks to Subliminal Frequency Hypnosis.
- 29 June - In the third video of the day, Chris reads yet another chapter from some godawful story because he thinks it will encourage people to give him money.