CHAPTER 2
A Transvestite is Born

The following morning I woke up with a wonderful feeling over me. I felt as if I had something to look forward to in my life. I literally sprang out of bed and went into the shower.

My cock still hurt a little and I had a sore groin from those extraordinary orgasms. But I felt invigorated. My mind was racing with all kinds of thoughts and emotions.

Was I really a freak? Do all kids go through what I had gone through the night before? Was I a pervert for getting aroused by my mom’s smell?

But at the same time, the idea of going through another dress up session filled me with eager anticipation.

I really hadn’t noticed how empty and lonely my life was up to that point. I barely had any friends. I never went out. All I did was watch TV, surf the net and play video games.

Suddenly, I had something to look forward to every afternoon. Dressing up in women’s clothes was a revelation to me. I wanted to walk into my mom’s closet to pick out the clothes I would wear to school. But I knew that was impossible.

I dressed quickly and went downstairs to have breakfast. My parents were still in their bedroom. Apparently, they had arrived pretty late, and they were still asleep.

I went to the fridge and poured myself a glass of orange juice. As I sat down and started drinking it, my mom came into the kitchen. She kissed me lightly on my head and started fixing some coffee.

She looked spent.

“’Morning, mom,” I said cheerfully. I was feeling fantastic. I couldn’t wait to get home that evening and go through her closet to try on some more of her clothes.

“You’re quite cheerful this morning.” She replied making an effort to stay awake.

“Do you want me to help you? You look beat.”

“We got home at 2:00 AM last night. I’ve hardly slept.”

I got up and started making the coffee for her.

“I’ll do that.” I grabbed the pot from her hand, and started filling it with water. She simply sat down and put her head across the table.

“Ooooh. I’m so tired.” She spread over the kitchen table and closed her eyes.

As I made the coffee, I would look at her from time to time, and I would notice how her nightgown would cling to her figure. I noticed how the nightgown would hug her at the waist and hips, but how the skirt flowed down. Her breasts were supple and firm and filled the top of the nightgown beautifully. As she turned her head over her arm, her weight shifted and I caught a glimpse of her nipples.

I started to get an erection and blushed. I felt embarrassed and ashamed. What was wrong with me? Was I falling in love with my own mother? That was sick. I knew it was wrong. But I couldn’t keep my eyes away from her.

I knew it was really dangerous. What If she opened her eyes and caught me staring at her breasts with a huge hard-on? I would spend the rest of my childhood in therapy. So I snapped out of it and put a cup of coffee in front of her.

“Thanks sweetheart” she simply said without even opening her eyes. “Have a good day at school, today.”

“Thanks. Bye, mom”. I ran out of the kitchen and went outside towards the bus stop.

As I sat on the bus, I knew my life had changed and it would never be the same. Everything felt and looked different. Suddenly I realized that I was staring a lot at girls. But I was looking at how their clothes fit. I checked the different styles of skirts, blouses and pants.

As I looked out the window into the street, I was noticing which women were wearing pants, which ones were wearing skirts, which ones were wearing dresses. I noticed if they were wearing pantyhose or had their legs bare. I would notice which ones had make up on and which ones didn’t.

Suddenly, I was noticing everything about women. How they wore their hair. How they wore their makeup. And I realized that I was noticing all these things to try and recreate them later that evening when I was home alone.

When I got to school, suddenly I was aware of every single girl around me. I saw how the skirts would cling to their waist, but drape down their legs. I would notice the way they walk, they way they move, and how their clothes would respond and sometimes enhance their movements.

The rest of the day was a blur. I didn’t pay attention to any of my classes, and all I wanted to do was to race home and try on some dresses.

After what seemed like an endless day, I arrived home at 3:00 PM to find mom waiting for me in the kitchen. She was wearing a green, plaid, pleated skirt with tall, black boots and a green turtleneck sweater that enhanced her breasts.

“Hi mom.” I tossed my backpack in the living room and went into the kitchen to kiss her hello.

“Hi, honey. Can I talk to you for a minute?” She asked in a very serious tone.

I froze. For a minute, I thought she had somehow noticed that her clothes had my semen, or something like that. My heart sank.

“Here. Sit down. Can I get you something to eat?” I wanted to die.

“No, I’m fine. What’s wrong?” I asked almost pleadingly.

“Nothing. I just wanted to talk to you about some things.”. I started to relax. “I wanted to thank you for helping me out last night with the laundry. And this morning with the coffee”. I was all ears. “It seems that you’re growing up really fast. Sometimes it’s tough on a mom to realize that her little boy is becoming a teenager. It makes her feel old.”

“You’re not old. Quite the opposite. You look great!” I found myself hitting on my mom, and she didn’t even realize it.

“Thanks, honey. But I was thinking that maybe you could help me out more around the house. You’re home a lot, and I got all these activities at your school and at the community center. If you could continue to help me with the laundry and cleaning up, I would really appreciate it”.

“Sure. No problem”. I was beside myself. Outwardly, I was calm and in control, but inside I was thinking to myself; “wow! Unlimited access to all her clothes every day with no interference”.

“Just don’t let it get in the way of your homework”.

“Don’t worry. I won’t.” I was feeling incredible. I was so glad and was so falling in love with her, that I decided to probe her to see how she’d feel if she knew I wore her clothes.

“You know, mom. I wanted to ask you something.”

“What is it?” She was genuinely intrigued and was giving me her full attention.

“Well, it’s kind of weird.” She frowned. “On the bus ride home, I heard these kids talking behind me. One of them was saying how she caught her brother dressed in his mom’s clothes last night. Then they found a bunch of love letters all addressed to his mother saying how much he loved her. The girl said that the entire family is in shock and they don’t know what to do with that kid.”

“Oh, my God. How terrible! Who is it?” she asked. Her face was in real shock.

“I don’t know. Just some kid at school, I guess.”

“That’s awful. They should put him in a psychiatric institution. That boy is sick. Imagine falling in love with his own mother… And wearing her clothes too. I only thank God that you’re normal. I don’t know what I’d do if I found you in my dresses.”

My heart sank. “Yeah. Imagine that…”. I was heartbroken. I couldn’t tell her what I had done, nor what I wanted to do. I couldn’t share my feelings about her. But at least I knew where I stood. I would have to be extra careful about my cross-dressing. “I wanted to tell you about it because I thought it was too weird.”

“It’s not weird. It’s sick. It’s perverted. It’s wrong. I can’t think of anything more repulsive than a man in woman’s clothing. And a son in love with his mother? Oh, God. I want to throw up. Whoever they are, please stay away from them, okay? Bye, honey. I’ll be back at six to start fixing dinner.”

She kissed me and left me sitting there. I was really sad. But at the same time that conversation snapped me back to reality. I decided to cope with the fact that I would never have my mom, but at least I could have her clothes.

With that, I went upstairs, and took off all my clothes, moving into her closet. I needed to make sure that last night’s events were not a dream.

I opened the panties drawer and pulled out a pair of white, satin panties and put them on immediately. Then I found a matching bra and I fumbled with it until I put it on. Then I opened the drawer were the stockings were and I pulled out a pair of taupe, nylon pantyhose. All of the feelings from the previous night rushed in and once again I found myself in heaven.

From there, I moved onto where the clothes were hanging neatly in racks. I started to look at everything, one by one, and finally chose to wear a pistachio green suit. That suit had a mini skirt and a jacket. I went to where the blouses were and I picked a white, spandex turtleneck blouse.

There was a pair of green pumps that I put on after that. I looked at myself in the mirror, and the girl was there again. Only this time, I felt that I really needed to put on some makeup.

I went to the dresser and started to put on some mascara and some lipstick. When I finished, I definitely looked like a young girl trying to imitate her mom.

I knew I didn’t have as much time as last night, and proceeded to jack off. Once again, the orgasm was fabulous. And once again, as soon as it was over, I got that weird feeling over me. Suddenly I felt like I looked stupid. Stupid and sick and perverted and my mom’s words seemed to ring true.

To distract myself, I fought off the impulse of taking off the clothes and wiping off the makeup, and instead I went into the den and started doing my homework. And just as I expected, a few minutes later, I found myself totally comfortable in my outfit once again.

I spent the rest of the afternoon dressed in that green suit until I looked at the clock. It was 5:30 PM. Mom would be coming home soon. I went into her bedroom, went into the hamper, and took out the panties she had worn at the party last night. Her wonderful smell was there. And as I ran my tongue over the crotch, I rubbed my hard cock against the skirt until I exploded in a tremendous and enrapturing orgasm that almost made me faint again.

I realized that the awkward feeling that came right after my orgasms was helpful so I could actually get these wonderful clothes off. Otherwise, I wouldn’t have minded getting caught.

As I started to take off the suit I noticed in horror that I hadn’t worn any protection, and that the panties and pantyhose were wet with my cum. I put the green suit away and ran into my room to hide the bra, panties and hose. I started to get dressed in my own clothes, and just as I was tying the laces of my shoes I heard the front door open and my mom walk in.

“Honey, I’m home. Would you give me a hand fixing dinner?”

“Sure thing, mom.” I made sure no tales of the make up were visible, then I went downstairs to help my mom with dinner.

As of that day, I knew my life would never be the same. I had to accept that I was a cross dresser. I enjoyed dressing in my mom’s clothes. And I also lusted after my mother. I found her to be the sexiest creature on earth and more than anything I wanted to penetrate her pussy with my cock.

But for now, I would have to accept the fact that she would never be mine and that the closest I’d get to her pussy, would be to lick the crotch of her used panties. After all, she had put me in charge of them. I couldn’t think of anything more rewarding.

As I walked down the stairs to help her with dinner I felt happy to face this new phase in my life. The years to come would be full of excitement and exploration.

But little did I realize, that this path would lead me into a future that I never imagined in my wildest dreams could be possible. It would put me face to face with my real sexuality.