After the difficult end to that relationship I had made a decision to continue on within the BDSM lifestyle. I spent some time in our local scene and several months later I met a very intriguing Domme at a local event. We hit it off pretty well and soon after I found myself in regular contact courting her.
She was quite a bit different than other women I had known, including my ex. Unlike my ex, this woman's dominance ran deep and completely to her core. She didn't just enjoy the kinky aspects of the lifestyle, she thrived on Femdom and making men suffer in pretty much every way imaginable. At the same time, she was a very caring and loving person. While I probably should have approached with caution, I threw caution to the wind and dove in head first.
During our courting period she asked me many questions about my previous experiences and wanted to know all of my deepest, darkest secrets and desires. When I told her about the punishments I had been receiving late in my previous relationship she could sense the great shame and humiliation it brought me while recounting those experiences and that drove her completely wild. She also happened to love fur and it turned her on.
I must have made a good impression because within a couple of weeks we began seeing each other regularly. Our times were split between going out shopping together or staying in for body worship and play. Although she had been part of the BDSM scene for a long time, forced feminization was new territory for her but she thrived upon it and took great pleasure in shopping with me.
She also had very few inhibitions about making things obvious in public. I still have rather vivid memories of an outing to a department store where we found this exact hat during the Christmas season. She put it on my head and made me model it for her with around a dozen women present within 20 feet of us. She told the sales clerk that she didn't trust mirrors so it was better to have me wear it for her.
I can't remember another time where I was blushing so profusely and I was barely able to speak the rest of the day.
During our private times she was a firm believer in exerting control over my sexual activities. Masturbation was only permitted with her present and I wasn't allowed to ejaculate during sex. Continuing on with the later trends of my ex, I was only allowed orgasm while dressed in women's clothing but she took things a step further, adding sweaters, skirts, and stockings in addition to items similar to what my ex had used. My masturbation outfit became a pink angora turtleneck sweater, a pair of pink satin panties, pink fishnet stockings, a fuschia micro skirt (that was so short it wouldn't cover my butt or genitals), a pink wool hat with a sparkly sequined snow flake on it and a large dangling pom pom from the top, a pair of huge pink fox fur earmuffs, a pink fur scarf, and a pair of pink wool mittens with fur cuffs.
She too would order me to masturbate while looking in a mirror while she watched over my shoulder and would tease my nipples and emasculate me verbally until I was nearly in tears. This would continue for 45+ minutes until I was granted permission to cum.
What she was accounting for and I had failed to account for was that after 2 years of only being allowed to cum in this fashion, her goal was to condition my sexual response. This became increasingly apparent when she introduced chastity devices into the mix after the first year and stopped having sex with me. At first she would wait to remove the device until after I was dressed but after several months she started removing the device before I was dressed. The first time she did this she noticed that I wasn't instantly hard upon the device's removal but once I started getting dressed I had a raging erection. When I was completely dressed she ordered me to masturbate and then hissed in my ear that she had "ruined" me and that now I wouldn't be able to get hard unless I was dressed as a sissy. I began to cry but she insisted I shouldn't worry because we would be together forever.
By this time we had made plans to live together and she began laying down ground rules for this to happen (chastity, dressed fully in women's clothing when home, etc.). Soon after a few major events happened in each of our lives and we ended up parting ways when she relocated.
It donned on me then that things would be much more difficult for me from there on out. Normal sex doesn't do it for me. Normal porn doesn't do it for me. I would only be able to get hard while dressed as a sissy and being humiliated or fantasizing about that.
4+ years later I feel I have finally come to terms with who I am now. I am a sissy... and probably always will be.