Like most people, they find the internet is a way to explore their sexual desires in private and with anonymity. I had no one to talk to about my need to wear women’s clothing. I didn’t know how to explore my sexual feelings and desires other than the web. I was still deep in the closet, and my parents wished I stayed in there forever.
Luckily my family wasn’t very clingy, and they left me alone in my room for the most part, especially at night. So, I could safely put on my makeup and dress up in my lingerie or dresses.
I would surf for porn, look at pictures, and read stories of like-minded people. I went to a few chat sites as well, most everyone was very accepting of me and the fact that I was a “sissy boy,” “fem boy,” “trans,” “t-girl,” or a “crossdresser”.
One night a window popped up like any other, but this was from a man named Max. After chatting for only a little while, I found out he was different from most. He was kind, yet firm. He was brutally honest and asked me to be the same. He asked me about my feelings dressing up as a girl. What I wanted in my life. Most importantly, he told me I was special. No one had ever thought or said to me that before.
Our relationship was very hot at the beginning and kept burning for months. Max controlled the speed of the relationship, and it was a slow build. I called Max, Daddy, from the very start, and he called me his baby gurl. I still tingle thinking about that.
Daddy seemed appropriate as he was forty-five, married, and had kids of his own.
Max was tanned and had a large shaved uncut cock. He was very fit and had an incredible body for a man his age. We would write stories to each other and send emails many times a day. He would give tasks: like go to the mall dressed as a girl, walk around with a dildo in my boy pussy. Outside of my house, I began to feel more comfortable in my female clothes and makeup. He was nurturing my need to dress as a woman and the need to feel more feminine. I was developing strong feelings for him. I knew he was married, and I was his dirty little secret, but I didn’t care. I was enjoying myself, and I was becoming more confident in my own skin.
One night, Max and I were skyping, and I was putting on a little show for him. I was dressed in a pretty pink corset with white stockings with pink bows. I had red nail polish on my fingers and toes. I was working on my makeup, and I looked gorgeous. My blond hair was just getting long enough to put in pigtails.
I watched Max on the computer screen, stroking his hard cock watching the show. I took my rubber dildo and started to suck on it, slowly up and down the shaft.
“Suck on my cock baby girl,” Max encouraged me on the screen.
I had been practicing and could almost take the entire cock without gagging.
“Daddy needs to fuck that boy-pussy,” Max instructed.
I took the dildo out of my mouth and got on my back and spread my legs and slowly inserted the rubber cock into my tight asshole. Max encouraged me as I was sliding the rubber cock in and out of my tight asshole. I was stroking my hard cock with the other hand. I was whimpering as my orgasm was starting to build.
Suddenly my bedroom door swung violently open. The lock that was on it came flying off. It was my father! His face was red with anger and confusion. He quickly scanned the room. The computer with Max jerking off on it. Women’s clothing was strewn around the room. And his son, dressed as a girl in pigtails with a huge dildo up his ass.
Confusion turned to anger that I had never seen in anyone before.
“What the fuck are you doing!” My father screamed.
He reached over and grabbed my hair and threw me violently to the floor. Shaken, I tried to get up, and he shoved me away and back against my desk. I started crying.
“Please stop hitting me!” I pleaded to him.
My father reached over and pulled at the corset and tugging on it, trying to pull it off. He shook me back and forth.
“What is the matter with you?” He asked as he shook me.
“This is who I am!” I told him through the tears.
“No, it isn’t!” My father said as he reached back and slapped with his open hand.
“No son of mine is a faggot!’ He added.
“This is who I am.” I pleaded again.
“Not in my house, you aren’t.” He answered coldly. “Get the fuck out!’
I looked back at him, shocked and sobbing. Just past him, in the hallway, was my mother. She just turned and walked away. I knew then, I was never going to be accepted by my parents.
I packed up my things that night and spent the night in a motel. I cried the entire night. It was hard to know that you had no choice in my feelings and that my parents would never be accepting of who I am, even though I was still trying to figure that out.
The next morning, Beverly was phoning. She was my best friend, Greg’s mother, and the only other person that knew about me.
I didn’t answer the first three times, but then I finally relented. She had heard from my mother that I was kicked out and that she called to tell me that I was welcome to stay with them as long as I wanted.
I stood pathetically outside of the motel with my three bags when Beverly pulled up in her SUV. She walked right over and gave me a robust and comforting hug.
“It will be alight.” She assured me.
We arrived at her house just after noon. My best friend, Greg, came up to greet me. Noticing my bags.
