The first time I was fucked was an epiphany. It was a complete realization that I needed to keep exploring my fem bottom side, but also a transformation to be penetrated and free. Having not been fucked before, I was a bit nervous, and certainly tight. My daddy and friend, who had been patient for far too long was ready to fuck me once and for all. He was a delightful cross dresser who I cherish to this day for helping me open up both literally and figuratively. On the fateful day after months of play dates where I learned to suck him and fall deeper into my sissy desires, I knew I needed to… Read more

The first time I experienced the joy of being with a trans woman sealed my fate. It was falls and I found an ad in the personal section of a local publication. You know the ones with all the x rated ads. Anyway, I remember having to connect by leaving a phone message. Seems so archaic now, but so we’re the early days as the internet started to take off. After making some loose arrangements we decided to meet one Saturday. I drove about an hour flip flopping from total excitement to complete nervousness. Thankfully, I didn’t turn around because I knew this was something I needed to experience.… Read more

As my desires have gotten stronger over the years, I often wonder how far I could take my fem side. I clearly have an inner femininity that burns inside me and craves to be developed. I didn’t always want to be the fem counter part with a male partner, but the more I plunge into my feelings, it becomes more comfortable. I love the idea of having a supportive older daddy that helps bring out the woman in me.… Read more

The first memory I have of being with a man wasn’t till I was in my 20’s. He was much older and living alone. He must have been almost 30 years my senior. I was very nervous, but he helped me relax and we eventually ended up naked in his bedroom. I remember how amazing it felt as I climbed on top of him, and the feeling of his large cock against my butt. He was rubbing mine with his hands against his velvety stomach. I wanted to make him cum so bad. I wasn’t ready for any penetration and it took me years to get there and has only happened once. I turned and fondled his big daddy cock and he ma… Read more

It seems with every passing day, I get more enamored with the thought of feminization, but it didn’t necessarily start that way. When I first discovered trans woman it took me by storm. Yes, I’d been long excited with dressing, but that came with fear and shame. What would people think? Could I ever open up? When I discovered the beauty of a woman who was brave enough to be her true self, even if she was born with a penis, I was instantly aroused. Yes, initially this was through online porn, which does fetishize trans woman, but I couldn’t control my attraction. Was I gay? I didn’t think so,… Read more

Like so many other dressers, I started young. I don’t remember when exactly, but I can’t remember a time when I didn’t crave to be fem. One of my earliest memories was having a sexually explicit book that I’d read at night. I always envied the young female protagonist hitchhiker. The vivid description of being picked up by a passing trucker and the huge bulge she’d notice in his pants, later to find out that his cock was a treat all it’s own. On those night quite reading in my room, I’d slip into a little pair of red panties and nighty I’d swiped from a friends cute mom. Laying in bed dreaming… Read more