Greg says he was offered threesomes throughout his past, but he always turned them down. One instance that he recorded in his online writings was with his bisexual high school girlfriend Shiree. According to Greg, after deciding to get back together, he asked her to "end her ties" with her girlfriend. He says she offered "alternatives", but he turned them down. (Source)
On January 31, 2011 Greg uploaded the video "Would Onision Have A Three-Way?". Greg says he would "never ever have a threesome based on my current state of mind." He explains, no matter how attractive an offer would be, he would turn it down because he finds it degrading to your current relationship. He says it's degrading to the relationship because "that relationship is no longer as strong as it once was because you just shared something that was supposed to be exclusive with someone else." He says dedicating his penis to once person is important to him. He adds if your partner is already entertaining in the bedroom, why would you need another person? "I think really it's just an insult to the relationship and an indication of your own sexual failures to resort to a threesome." He says he' been offered threesomes in the past, but he turned them down. He says he only makes love for love and he could only be in love with one person at a time. ($ource) When he uploaded this video, he had been secretly dating then girlfriend, Shiloh, for over a month.
Later that year, Greg release his second self-published book This Is Why I Hate You. In the book, Arthur, the main character he based on his dark side, dated a bisexual girl that had a lesbian girlfriend. The three characters would participate in, and/or watch each other, engage in sexual activity. Some began to speculate this was a fantasy of Greg's and that's why he was allowing his wife to date women, in hopes that he could participate sexually.
In January 2016, this fantasy came true when he, Lainey, and her girlfriend Billie had a threesome, but Lainey stopped it when they got to third base. Greg says he wanted to go further and was disappointed when Lainey said she did not want to have another threesome in the next few days. He says he felt like marrying someone that is bisexual was a "dream come true" because "seeing two women make love to each other is absolutely beautiful to me." ($ource)
Following this sexual experience, a series of events took place that ended with Billie out of the picture.
In the summer of 2016, Greg began bragging online about having "multiple threesomes" with two "amazing individuals" and would say the internet could try to shame them all they want. (Source) It was soon revealed Billie was back, so most likely Greg was talking about having threesomes with his wife and Billie.