My name is Chris, and I had just separated from my wife of several years (Stephanie) and she had temporarily moved to her parents' place a few hours away. She had packed up some essentials, but left most of her stuff behind, planning to come back after getting her own place.
I was left home alone with a lot of time to think about what went wrong. One thing she said to me in one of our last fights kept replaying in my head. "Maybe you're a fag and that's why you can't keep it up or ever last long enough give me an orgasm." I didn't respond to that (which I think was more designed to hurt me than be a real accusation about my sexuality), but she'd hit closer to the mark than she probably realized. The truth was, I had fantasized about being with another man since middle school, and probably masturbated more times during my marriage to the thought of being with another man than the number of times I'd actually made love to my wife.
While part of me wanted to try to get her back and make it work, part of me felt like I had failed at being a heterosexual husband, maybe it was time to try something new, and maybe I had been lying to myself that I was bisexual but mostly straight who just had some strange fantasies that he'd never act on. I worked up some courage and registered on a dating site as bisexual, and after some deliberation, listed myself as a versatile bottom (although almost all my fantasies involved me exclusively as a bottom, maybe I couldn't fully admit that online). After a few weeks, I got a message from a good looking guy. (It was weird for me to think that, because despite all my fantasies, I never found myself actually attracted to men in real life, and didn't really consider myself "emotionally attracted" to men.)
His name was Jim, and he was about 45 years old, 6'4, 225 pounds, dark hair and a salt and pepper, neatly trimmed beard, and said he was a psychologist. (I on the other hand was a fairly petite 5'8", and about 155 pounds, with no facial hair and about 35 years old.) His profile said he was a top. I guess you could say he was a "bear" and I was a "twink" (which is embarrassing to admit). My heart was racing when I agreed to meet him for dinner on a Friday night.
We met at the restaurant and I was a little self-conscious when he gave me a hug and a kiss on the cheek before we sat down. I had never even told anyone that I had any gay fantasies before, and here I was, getting kissed by another man in public! We had a nice dinner and good conversation and I found myself surprised to enjoy his somewhat flirtatious tone and obvious interest in me. He was definitely acting like "the man" and pursuing me as if I was "the woman," which was something I'd never experienced before and found both exciting and a little strange. He was very masculine (and I wouldn't have even known he was gay outside of the circumstances), and he even picked up the check like a real gentleman! This really turned me on, because it felt like I was no longer trying to project the "strong confident straight man" I had spent my whole life striving to show the world. Jim acted like he knew who I was deep down (a bottom) and made clear that he was the one in charge.
I had come by an Uber and he had driven, and he offered to give me a ride back to my place. I offered for him to come in and join me for a drink, and he parked his car in my attached garage (my wife had taken our car with her when she left).
Jim had asked me at the restaurant about my separation and pending divorce, but now he started asking me some more personal questions. "What was the first fantasy you had about another man," he asked over a beer on the couch. He was sitting close to me and had put his arm around me and my heart was racing. Was I really doing this?
I asked if this would be private between us, and he promised it would and he really put me at ease, and I figured, why hold back at this point. He's here, I admitted online that I was a bottom, and I might as well be honest and open for a change.
I replied, "I always fantasized about being wrongfully sent to prison, and being cellmates with an older man. The man would notice how terrified I was at being small and vulnerable and clearly not knowing how to fight, and would tell me a very self-serving, but also somewhat comforting, narrative about how there are (and have always been throughout history) people playing male roles and female roles in every setting, even when there are no women around like in a prison, or in the Roman army, or on a Viking ship at sea. He would ask if I had ever thought about what it would be like to be a woman, and I would sheepishly admit the truth (yes), and he would then make his offer. For my time in prison, when there wasn't going to be any judgment from the rest of society, he would tell me it was my opportunity to be a "woman" for a few years and experience something I had wondered about before.
