When did I start feeling the need to dress in women's clothing?

I am sure it is similar to most people. It started early on when I found a pair of my mother's panties on the bathroom floor. I had just stepped out of the shower, and I slipped them on. They were sheer silk black panties. They felt cool to my skin, and I immediately became erect. I heard my mother coming, so I quickly took them off and threw them back onto the floor, but that day was etched in my memory forever.

I couldn't stop thinking about her panties and how they felt wearing them. The next day I opened the clothes hamper, and to my delight, I saw a pair of my mother's dirty panties right there on top. I grabbed them and ran back to my room. I lifted them to my nose and breathed in deep. I became instantly hard, and then I took the panties and wrapped them around my cock and began to masturbate until I quickly came all over them.

I looked down at the cum covered panties, not sure what to do. I decided to try them on. They felt amazing! The wetness of the cum and the silkiness of the fabric made me feel alive.

Two days later, my mother mentioned to my sister if she'd seen her panties. Little did they know that I was wearing them under my jeans.

Over the next few years, I would wear my mother's panties under my clothes and would eventually wear one of her bras as well. She was rather large breasted, so it didn't fit that well, but I enjoyed wearing it.

I would stare at myself in the mirror and pose; it always made me happy, but also guilty. I knew my parents wouldn't approve of me wearing women's clothing. My father is a very masculine man and loves sports and didn't think much of sissies, and although my mother was not overly religious, she would frown upon my behavior or this phase I was going through.

I searched the internet, looking for answers to who I was. It was like diving in a vast ocean, and I was a minnow. I eventually found my way to forums and groups of like-minded people.

Most were very helpful; some were downright evil.

I learned proper makeup tips from other trans women. Makeup has a considerable learning curve. In my first attempt, I looked like a cross between the Joker and a Kabuki Warrior. I did get better, though.

I met three beautiful trans women online that I am still close friends with. I met quite a few men, not surprisingly. Most were straight men with curiosity. They would ask me to dance for them and masturbate on the webcam. I did and enjoyed it as it turned me on as well. A couple of men were quite sincere. I enjoyed chatting with them and, of course, putting on a show. During this time is when I learned that my asshole was extremely sensitive. I loved inserting my hairbrush in there, and it would make my orgasms more intense.

It was at this time when I met Max. He was forty-five years old and married, but he was different than the others. He was strong and assertive, but never abusive.  He was nurturing and loving and always called me his baby gurl. He had an amazing tanned body and a thick uncut cock. More about Max later.

I knew I couldn't continue to steal my mother's underwear, so I went over to my best friend Greg's house. I was on a mission. Greg's mother Beverly was beautiful, very sexy, and was about my size. She always dressed elegantly, and I assumed she would also have beautiful underwear to match.

Greg and I were alone playing video games. He got a call from his girlfriend, and I took the opportunity to sneak upstairs to his parent's bedroom. I opened his mother's wardrobe, and I saw a broad array of panties and bras. I'd hit the motherlode! She had many different colors and styles; it was almost overwhelming. I settled on a pink set of panties and a matching bra. I saw a garter belt and black fishnet stocking as well but decided it would be too much! I stuffed the panties and bra into my pocket and ran downstairs to join Greg.

I couldn't even focus as we played. I couldn't stop thinking about the underwear in my pocket and, more importantly, the garter and stockings upstairs.

I decided that I couldn't leave without them, and just before I left, I ran back up and snatched the garter and stockings.

I got home to find that my parents and my sister were going to a school function for her and would be out for hours. They were only there for an hour more, but it felt like hours before they left. I couldn't wait to see my newly acquired treasure.

The minute their car left the driveway I bolted upstairs with lightning speed up to my room. I stripped down naked in a matter of seconds. 

I stood there naked in front of the full-length mirror. I had just turned sixteen, and I was developing quite a bit of hair on my chest and genitals. I decided that for the full effect, I would need to shave the hair from my body before I put on these elegant, feminine clothes.

In the bathroom, I shaved my legs, which was a little bit more complicated than I thought, but I managed to contort enough to complete the task. Then my chest and armpits. I shaved around my cock and balls, leaving just a small "landing strip' of pubic hair above my hard cock.

Back in my bedroom, I examined my newly smooth body in the mirror. My hands trembled as they moved across my body like a lover's hands. I have never felt so turned on in my life.

I pulled my treasure from my pocket and arranged the underwear on my bed. I sat on the edge of the bed and picked up a stocking and rubbed it gently on my cheek. Then I turned to the mirror and rolled up the hose, pointed my toes, and slowly pulled the stocking over my foot and up my smooth leg. It was a slow striptease but in reverse. Grabbing the other stocking and did the same to my left leg. I then grabbed the pink lace panties and pulled them on. Women's panties are not made to accommodate a man's cock, especially when it is hard, but I did my best.

Next was the garter belt. The orientation confused me at first, but a quick internet search solved all my problems.

The bra was the final touch as I turned toward the mirror and saw the first step of a pretty young lady forming.

For the next year, I always wore women's underwear under my male clothes. Shaving my body smooth was easy enough to hide from my parents, but my red nail polished toes nails were a sometimes difficult cover-up. I started to wear black eyeliner, black nail polish, and a little longer hair, disguised as my new 'goth look.'

I decided I needed a dress for the next step of my evolution. So, I went back to my friend Greg's house while they were away.  I had a key, so I let myself in and went up to his parent's bedroom.

Greg's mom has a wonderful selection of dresses and sexy outfits. I saw her in this lovely black skirt and dark green blouse that I went for first. I tried it on, and it fit perfectly. I looked in the mirror and saw an elegant lady standing before me, but she needed something. She required high heel shoes. I went back to the closet and found some sexy black heels with an open toe.

Back to the mirror to examine the completed look. I was in heaven.

Pulling off the skirt and the blouse, I went back to see if anything else caught my fancy. I stroked my hard cock as I went 'shopping' for another outfit. I found a very sexy red evening dress. I held it in front of me and knew it would look amazing on me.  I looked around for shoes to match the dress when I came across a large wooden chest.

I opened it and found a large assortment of sex toys. Leather whips, handcuffs, and vibrators, as well as three rubber cocks of varying size and a rubber arm! Beverly and her husband were quite kinky, I thought. I took the medium-sized cock and licked it and put inside my mouth, sucking on it.

I stepped back into the bedroom, dress in one hand, rubber cock in the other.

"Sam, what are you doing?" A voice from behind me spoke.

I wheeled around panicked. It was my friend Greg's mom, Beverly!

I wanted to run, but I was frozen. I wanted to throw up, but I couldn't air. I just stood there, dumbfounded.

Beverly looked around the room, looking more confused than me.

"Sam, what are you doing here?" She asked again.

I couldn't speak. I just stared at my friend's mom.

"Go downstairs and wait for me," Beverly ordered.

I quickly moved past her, handing her the red dress and the rubber dildo as I passed.

I waited in the living room for what seemed like forever, what was she going to do? Would she call the police? Call my parents? I wasn't sure what would be worse.

I was crying my eyes out and shaking when she finally came down with my clothes in her hand.

She immediately hugged me and told me everything would be alright.

Beverly held me for over thirty minutes until she finally spoke.

"We need to talk," she said obviously but in a motherly tone.

"Yes," I stammered.

Beverly started, "We both have had secrets revealed today."

I nodded.

"Let's start with you," she said gently, "how long have you liked to wear women's clothing?"

I hesitated, but she put her hand on my knee and assured things would be okay. She looked at me, wearing her stolen bra and panties.

"We are sharing a lot already," she smiled.

I explained my journey to her, and she nodded and smiled and was quite supportive.

"I only stole from you, because I didn't have access to any other clothing that would fit me," I explained.

"Do you consider yourself a he or a she? Beverly asked gently.

"I believe I am bisexual, and for right now, I like dressing up as a woman, and I don't know what to call myself yet," I told her.

"Okay, we will call you she when you are dressed as a woman, and he when dressed as a man until you decide," she told me.

"Let's find you something for you to wear," she said, grabbing my hand and leading upstairs. "If I give you the clothes, they can't be stolen."

When we got back to the bedroom, she started to pull clothes from her closet for me to wear, it was like I was on a shopping spree.

I think I tried on every bit of clothing in her closet. I was exhausted but exhilarated.

After Beverly and I were finished, I had four new outfits and three sets of new lingerie, including the green blouse and the red evening dress.

Beverly looked at me and smiled, as she tied up the last bow on the black lace corset I was wearing.

"You look very pretty, Sam," Beverly complimented me.

"All of this has made me extremely horny," she admitted. "I see you are quite turned on as well," she added as she pointed to my hard cock protruding from my black panties.

"Would you like to watch me masturbate, Sam?" Beverly asked.

"Yes," I gulped.

Beverly pulled her dress up over her head. She turned her back to me and had me unhook her delicate pink bra. Beverly turned back to me and smiled. I finally got to see her supple breasts and her hard-brown nipples. She reached forward and grabbed hold of my hard cock and slowly stroked it up and down and gave it a little squeeze. Smiling, she pulled me to the king-sized bed. Beverly crawled on the bed seductively.

"Sam, can you pull my panties off for me?" She asked me in a very sexy voice.

I reached over, putting my fingers in the waistband and slowly pulled them over her ass and down her legs and passed her very sexy feet. She slapped her ass with her hand.

"You can spank me if you want Sam," she said.

I smiled and slapped each cheek with my hand. Beverly giggled and moaned.

Beverly then flipped over on to her back. She then spread her legs and lifted her bare feet into the air, pointing her toes. Her fingers moved down to her pussy, and I was pleasantly surprised to see she was shaved smooth down there and she had large labia.

She told me to move close to her and stroke my cock. I watched her intently as her fingers rubbed her clitoris. She pinched her nipples and moaned. I stroked my hard cock as I watched this woman start to moan louder and arch her back. Suddenly she began to shake as she announced she was cumming! She screamed a guttural scream as she came. I watched her as the tremors started to subside. It was the most erotic thing I had ever seen, and I stroked my cock even faster and was closer to cumming as well.

"Wait, I want to watch you cum," Beverly told me breathlessly.

That statement was too much for me, and I came immediately, all over my corset and chest, and even on my face.

We both just lay there quietly, with only the sounds of our breathing.

"That was amazing, Sam," Beverly told me breathlessly. "I had so much fun!"

"I did too," I told her enthusiastically.

Beverly took off my cum stained corset and told me she would have it cleaned for me, then she neatly folded all of the clothes into a small suitcase, while I dressed into my male clothes. I looked over to the rubber cock that was still on the dresser. Beverly smiled and threw it into the suitcase. I smiled happily.

"Now you should go, I am quite horny now, and I am going to need to masturbate again before Greg gets home," she stated matter-of-factly.

I raced home with my new bounty and at least someone close to me, knowing of my secret.