Anna Meets Megan (Part I) by Anna V. Hedge (avhedge@yahoo.com)
Chapter 1
My name is Anna Hedge. Well, that is the name I go by when dressed as a woman. Yes, that means I was born a guy. Since I can remember I've liked wearing women's clothing. It all started when I was 6 and I ventured into my mom's room and found a pair of gray nylons. I just had to try them on. After all, I had seen my mom wearing them in the past. The years went on until I found myself as a 21 year-old college student wondering about my sexuality.
After several battles trying to decide whether I was a transsexual or cross dresser that included several clothing purges, I decided to stop thinking so much about it and to enjoy myself. I started to buy clothing, makeup, wigs, breast forms, and so on online as to avoid the public eye. I would work and go to school during the week, and on the weekends I would transform myself into Anna, a lovable 21 year-old college girl.
One Saturday evening, as I was enjoying myself as Anna, I noticed that the trash needed to be taken out. I started to remove my attire when I decided that it was time for Anna to venture outside. I took off my pleated skirt, my wig, breast forms, and my high-heeled oxford shoes. I put on a sweatshirt over my blouse, and a pair of sweatpants over my nylon clad legs. A pair of socks covered the rest of my feet, and a pair of tennis shoes finished the outfit. I figured the makeup might give me away so I decided to take it off, except for the mascara and the blue nail polish. All in all, it was a very covered up Anna that was about to meet the outside world.
I grabbed the trash bag, opened the door to my 2nd floor apartment and stepped outside. I descended the stairs and headed straight for the trash bin. Every step was full of excitement. As I dumped the bag I noticed my neighbor's car starting to pull up. I was so glad that I had never met her. I turned around and started back when I heard the car door close. I moved as fast as I could. As I reached my door, a voice said:
"Hi!"
I turned around and returned the salutation as she kept walking towards me.
"It's nice to finally meet you. We've been neighbors for almost a year now and we'd never spoken." She continued: "I'm Megan."
As I looked up I noticed that her green eyes were staring squarely at me. Her blond hair flapped against her lightly made up beautiful face.
Forgetting about the nail polish on my nails, I extended my hand and said: "I'm Allan."
As we were shaking hands her phone could be heard ringing. She smiled and said: "I better get that. Nice meeting you."
"I'll see you around," I said as she opened the door to her apartment and rushed inside.
As I entered my apartment, the realization that I was wearing mascara and nail polish finally settled in. Had she noticed?
Chapter 2
A couple of weeks had gone by when on a Friday evening, as I was coming home from work, I saw her walking with mail in hand. I looked up, and with a big smile said:
"Hi!"
"Hi Allan. How you've been?" she asked.
"Busy. Working and keeping up with school work," I said. "How about you?"
"Same. I can't wait 'til next week for Thanksgiving. I get to go up north and take some time off at my parent's cabin."
"That sounds like fun. Listen, I have to get going. I have a paper due tomorrow. Talk to you later.
"Alright. Take care...oh, and if you ever need some help...with anything, just let me know."
What did she mean by that? What kind of "help" could I need? You had to know. But how?
She must have noticed the look of surprise that I had because she smiled and got really close to me. She proceeded to whisper to my ear:
"I know your little secret. Why don't you come up to my place and we can talk about it."
She took my hand and guided me to her apartment. I was speechless, yet at the same time I was feeling excited that a girl knew about my desire to be a girl.
"So, tell me about your girl side," Megan said as she took a seat.
I then told her about my childhood and the repeated incidents where I just "needed" to dress as a girl to feel good. About the countless times that I took clothes from my sisters and mother-in-law to satisfy my needs to look like a girl for a little while. About the time my dad walked into my room as I was putting on make-up and wearing my step-mom's clothes. About me walking out in my sweatpants with my bra, panties, and nylons the day we met.
"I'll tell you what, why don't you go up with me to my folks' cabin next week, and we can have a girl's only weekend?" Megan asked as I finished telling her about Anna.
"That sounds like fun."
Chapter 3
The day before the trip Megan stopped by and took me shopping. A dream come true. We got home after an extensive shopping session. Megan told me to pick an outfit and to pack the rest for the trip.
The next day I woke up to Megan knocking on the door.
"It's time to get you ready for the trip. Now take off your clothes and let's get to work"
As I stood naked in front of this beautiful woman, she applied a hair removal lotion in every area of my body that showed a sign of hair. Thankfully, I wasn't the hairy type. As soon as the hair was gone, she gave my hair a slightly more feminine look by doing some cutting and trimming followed by dying it. I was then instructed to take a shower. As I came out of the shower Megan was ready for step 2 of the transformation.
She helped me into my black satin bustier, which minimized my waist once it was tightened. The breast forms made me a B cup. The black silky panties and garter belt started a chain of emotions that ended up with me getting rock hard.
"Well, look who's here," she said while staring at my erect penis. "We need to hide this bulge, unless you want to tarnish your girly image."
As she said this I tucked my penis between my testicles and pulled my panties up so that the whole package would remain in place. I followed this by clipping on my stockings to the garters. To this Megan added:
"It is a good think you painted your toenails last night. Now let's take care of those hands and that lovely face."
The next half hour consisted of Megan giving my hands a manicure that resulted in the most gorgeous French Tip that I had ever seen on anyone's nails. She then took care of my makeup. She started with plucking my eyebrows to a distinct arch, followed by foundation, eye shadow, mascara, blush, and lipstick. She then finished up my hair by styling it. I then went over and put on my metallic gray silk blouse and my dark brown pleated skirt. As I was putting on my platforms, she walked towards me and pierced both my ears with a pair of gold studs. She took a couple of steps back, and said:
"You make a beautiful girl Anna."
"Thanks," I blushed.
"Let's get going girlfriend."
To be continued...