I have this old friend that I went to college with that I have not seen in 20+ years. We will call him 'Sam' - not his real name but important that it is a name commonly used for both male and female. A mutual friend told me that he came out as trans and I was shocked because he was not what I think of as the typical soyboy... I would have classified him as 'deplorable.' Last I talked with him he was married and expecting children. So I decided to reach out to him. I dug around and found some contact info... turns out he had moved a few years ago and was back in my area. He sounded like my old friend on the phone. We decided to get together for a beer. So I go to the bar and there he is... wearing jeans, sneakers, a tube top, lip gloss and eye liner and 5 o'clock shadow from his beard... I had many questions for him. I told him I thought it was a joke when I heard he came out trans. He laughed and told me his story. His marriage lasted until the kids were out of the house in college. He and his wife 'drifted apart' and he admitted that in the end they only stayed together for the kids. Once the kids left there was nothing keeping them together. They separated and he moved back to my area to be close to his parents who are getting on in years. At his job he was leading a small team and the company was growing and hiring. With the growth came new HR policies and when he tried to make a job offer to a candidate he was told he could not... his hiring was subject to diversity hiring rules and because his team had more guys than women, he HAD to hire a woman. He said he was pissed but not enough to hire a lawyer... and he did not even have standing etc... So he decided to come in the next day in a blouse and lipstick. He claimed to now be a woman and therefor his team had no 'gender inequality' and he could hire anyone he wanted. I laughed my ass off... but then asked him why he was still in drag? he explained that he had been planning on just doing it until he had his new hire actually start working and then he would 'decide he was a man again'... but that by that time he was getting way to much pussy to ever go back. Wut? He explained that once he started 'presenting a female gender expression' there were a bunch of 'man hating femanazis' (all his words) that suddenly wanted to talk to him and that many of them were completely cock starved. "I treat them exactly like all the men they hate would and they love it." He claimed to be getting more action then when we were back in college. He said "Look, after my wife and I separated I tried to get back into the dating scene. For a 50 year old guy, even being in good shape and well off financially, it was a ghost town. As a 50 year old trans lesbian I get enough action to be picky. I'm currently in a causal relationship banging a cute girl 20 years younger than me... so fuck it, I'm a trans woman." I laughed and told him it still makes him a faggot. He laughed. We drank a beer. It was weird. I really don't know what to make of this.