My Transition - Sex Stories

My Transition

My transition into male sex occurred a number of years ago after my first wife passed away following an extended illness. She had been unable to engage in sex for some time, and so I dealt with my physical needs the best I could, mostly through chronic, habitual masturbation. The months following her passing were very difficult for me emotionally, and I was having a hard time dealing with the grief, and the guilt. I had periodically struggled with bouts of guilt since high school, when I began to use masturbation to help deal with stress and insecurities. Back then, it was referred to as “abusing oneself”. I tried to stay busy and exercise to manage these urges, but when that did not work, masturbation (usually in conjunction with anal stimulation) became my “drug of choice”, as it were. I thought marriage would alleviate the need for this, and it did, for a while. But, compulsive, addictive behaviors are hard to break, and I found myself despairing over my lack of self-control. An even greater threat to my battered conscience was my growing desire for close physical intimacy with another male. Throughout my life, my traditional Southern upbringing and church teaching consistently taught me that such desires and behaviors are, at best, morally disordered, and at worst - well, you get the idea. Right or wrong, this was poured into my foundation from the very beginning. So, it should not have come as a surprise that this would be a source of emotional turmoil, especially ...

... when these thoughts occasionally gave way to outright craving for sexual union with a male lover. My taste for male sex (no pun intended) had been awakened some years earlier by an experience involving anonymous sex through a gloryhole at an adult video arcade, an experience for which I had repented profusely and repeatedly. I tried repressing these feelings as best I could, marshalling all of the Stoic resolve and spiritual strength that I could muster. But, in the end, it amounted to little more than token resistance. I could never share this struggle with anyone, or so I thought. It was during this period I was befriended by a fellow from church named Ken, whom I discovered was also a widower. He was a soft-spoken guy, about twenty years my senior, with a few extra pounds and a gray goatee. I learned that he had been in the ministry at some point, but had since retired. I can’t explain why, but I found myself attracted by his winsome personality, easy-going demeanor, and strange twinkle in his eyes. He invited me over to his house for dinner one evening, and I accepted. Following dinner, we were seated on a couch in the living room, sharing our respective stories and experiences. He seemed like a wise father-figure, and I felt free to express my thoughts and feelings. I even felt safe to share some of my secret struggles. During the course of doing so, I broke down, whereupon he slid over and held me in a strong, manly hug. I embraced him in return, and as my tears began to ...