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.

“What’s up?” Greg asked.

I hesitated with my answer until Beverly spoke up for me.

“Sam’s parents found out Sam was bisexual, and they kicked him out,” Beverly explained, the partial truth.

“That’s shitty, man,” Greg said, and added,  I didn’t know you were bi, man.”

“Is that okay?” I asked cautiously.

“Yeah, for sure,” Greg said. “I kind of knew it already.”

“What do you mean?” I asked.

“Well you look at girls and guys the same way, you know with that “I want to fuck them look,” Greg said.

“Greg, take Sam down to my craft room, that is where Sam will stay,” Beverly told Greg and added. “For as long as you want, Sam, Okay?”

“Okay,” I told her and smiled.

Later that night, I was getting things ready in my new room, sitting on the day bed when Beverly knocked and came in.

“Getting settled in?” She asked.

“Yes. Thank you so much for everything. “I told Beverly.

“No problem, Sam.’ She answered.

Beverly hugged me lovingly.

“Thanks for explaining it to Greg,” I told her.

“That’s okay, but you will need to tell him the truth.” She said.

“I know, but what if he hates me afterward?” I asked.

“You need to trust him as a friend, he is a good person, I am sure he will understand,” Beverly explained.

“Okay.” Was all I could muster.

“Everything will be alright in the morning.” Beverly comforted me. “Now lie down and get some sleep, you must be exhausted.”

She tucked me under the covers and then gave me a, not so motherly kiss on the lips.

“Good night.” She said as she closed the door.

I fell asleep right away.

The next day, everything was so much better. Greg and I hung out and played video games for hours. Although weighing heavily on my mind was how to tell Greg about me dressing in woman’s clothes and being a femboy. 

I talked it over with Beverly, and we decided it was best to just show him. So after dinner, Beverly helped me get dressed and do my makeup and hair. After we were done, I looked in the mirror, and I had to admit I looked great.

I followed Beverly into the family room where Greg was on his phone.

“Greg, Sam has something to tell you,” Beverly announced.

Greg looked up as I stepped out from behind Beverly.

Greg didn’t recognize me at first, but then the realization hit.

“What the fuck?” Was his first response.

I immediately had a fight or flight response. I decided to fight.

“I am a bisexual, but I also like to dress up as a girl,” I stated.

“I don’t get it?” Greg said, confused.

I looked back at Beverly.

“I will let you two figure this out. Call if you need me.” Beverly said as she left the room.

“I like dressing as a girl. This is really why I got kicked out," I explained.

“You’re a tranny?” Greg asked.

“Is that what I am?” I asked.

“You don’t know?” Greg asked back.

“No, I am just trying to figure it all out. I hope you are okay with this.” I told him.

Greg paused for what I thought was an eternity and finally spoke.

“Yeah, I’m okay. It’s just going to take a bit.” Greg said.

“I understand,” I said.

“What do I call you?” He asked as the thought just popped up.

“Samantha or Sam,” I told him.

“Well, that’s convenient,” Greg said, smiling.

There were a few minutes of awkward silence until Greg spoke again.

“Fortnite?” Was all Greg had to say.

“Yes!” was my quick and happy response.

The rest of the night was the same as before, good friends having fun. Just this time I was wearing a blouse and skirt. I was so relieved and happy!

At the end of the night, I went happily bounced back to my room. I opened the door to find Beverly naked on my bed, playing with her pussy. I closed the door behind me.

“I am so sorry, Sam, I tried to control it, but I need you to fuck me!” Beverly said lustfully.

I pulled down my skirt and opened my blouse, and moved quickly to the bed. Beverly reached and put her arms around my waist. She kissed my stomach and trailed her kisses down to my panty cover cock. She pulled down the waistband of my panties, exposing my very hard shaved cock. Beverly smiled up at me and then took my cock into her mouth!

Beverly expertly sucked on me, taking me deep into her mouth with ease. It was the most amazing feeling of my young life. Then, Beverly fell back on the bed and spread her legs.

“Fuck me right now, Sam!” Beverly urged.

I took my cock to the opening of her very wet pussy and quickly pushed it in. She moaned as I entered her.  I began to piston my cock into her, the rhythm between us was almost instant. Beverly spread her legs and grabbed her feet.

“Give it to me, Samantha! Fuck me!” Beverly cried out.

I started to pound her even faster. She began to moan even louder.

“Fuck, Coming!” She announced.

Beverly started to spasm violently. It was like she was possessed. She came for almost a minute before she regained control again.

This was too much for me, and I told her I was going to cum.

“Cum inside me, it’s alright.” She told me breathlessly.

A few more strokes and I was shooting my hot load into this beautiful woman’s pussy. The best orgasm of my life.

We laid together in each other’s arms for a while before she got up to get dressed.

“Samantha, I am happy you are here. This won’t be a regular thing, okay?” Beverly told me.

“Okay,” I answered.

Beverly closed the door, and I drifted off to sleep.

Things were indeed going to get better.