Anna Meets Megan

By Anna Hedge

Published on Sep 22, 2001

Transgender

Anna Meets Megan: Part II (avhedge@yahoo.com)

Part II: Chapter 4

The drive to the cabin was pretty much uneventful except for a quick stop at a rest stop. I had asked Megan to stop since my bladder needed to be emptied. As she pulled over at the rest stop, she turned around and asked me:

"Do you want me to come with you?"

"Nah. I think I got it."

I opened the door, grabbed my purse, and stepped out. I looked around the rest stop looking for anyone that might be looking my way. I smiled, as nobody seemed to notice me, and walked confidently towards the bathroom. After taking care of business, I washed my hands and touched up my makeup. I walked back to the car, and upon hopping back into the car; Megan looked my way and said:

"Someone's happy. And by the way, good job with the lipstick."

"I learned from the best," I replied.

Upon arriving to the cabin, Megan lead me to what was to be my room for the duration of my training. The room was most definitely a girl's room. The walls were painted white, but the decoration of the room had a feminine accent. The bed spread, with its light pink flowers made me feel even more girlish. Also, a beautiful vanity table stood on one side of the room.

"This is my room. It's looked this way since I was a little girl. You'll stay here, and I'll sleep in my parent's room right across the hall," Megan said.

"I love it, thanks."

"Why don't you jump in the shower? I'll unpack for you and when you get out we can start your training."

As I nodded Megan pointed to the bathroom at one end of the room.

"There's towels and everything you need in there."

As I showered, I admired the beauty of my shaved legs. I stepped out of the shower, and began to dry myself. I stepped out of the bathroom and found a white bustier, a pair of pink panties, and a pink silk nightie waiting for me. I put on the attire that Megan left for me, and before heading out of my room, I went back to the bathroom and picked up my breast-forms. I place them in the cups of my bustier, and with a big smile on my face (and a jiggling sensation on my chest) I walked down to the kitchen.

Megan looked up as I walked down, and said:

"Hello beautiful. It looks like everything fit perfectly"

"Actually, they are angelic. Thanks."

"No problem sweetie."

Megan then grabbed my hand and led me back to my room. She then told me to wait a minute. I looked at myself in the mirror as Megan walked to her room and back to mine. She came in holding a strap-on dildo. With a big grin on her face, she said:

"It is time for this girl to learn how does it feel to be a girl"

As she said that, she took off her clothes and strapped the dildo to herself. Her nipples had gotten rock hard. With the sight of a beautiful woman in front of me, and the rubber dildo pointing my way, my penis became rock hard. Megan looked up, saw my hard cock that was trying to be let out of its confinement, smiled and said:

"Honey. I see you can't wait for Megan to make you a woman."

With that said, Megan moved my way and removed all of my clothing. She then grabbed my rock hard cock, and guided me towards the bed. She released her grip and turned me around.

"This might hurt a little bit at first, but I can guarantee you that you'll be begging for more of this at the end of our weekend."

She then moved the rubber dildo into my hole. The initial penetration caused a couple of tears to roll down my cheeks. Soon enough, the pain turned into joy as Megan began to pump the dildo into my hole, and I began to have an orgasm. As she continued to pump, my penis became rock hard and I shot a load as Megan reached her orgasm as well. She kept on pumping in the cock, until her orgasm subsided and she finally retrieved what was now the object of my affection. We both laid exhausted on the bed. She looked at me, and kissed me. Her tongue playing tricks inside my mouth, she finally backed out, and told me:

"Good night Anna."

With that she turned the light off and we both embraced and fell asleep.

Chapter 5

The morning sun and a slight ache on my ass woke me up the coming morning. As I looked around, I noticed that Megan wasn't there. As I got up and went to relieve myself, the slight ache I felt on my ass got magnified. Megan walked into my room as I was walking out of the bathroom.

"Good morning sunshine. Are you ready for your morning workout?"

"My morning workout? Sure, I guess I could use some exercise," I replied.

"Look on the top drawer for that leotard we bought for you. And don't forget to put on your breast forms with the sports bra."

I went over and found my workout clothes. I put on my panties and my sports bra, with my breast forms of course. The leotard was a long sleeve purple thing that I had fallen in love when I saw it at the store. I then put on a pair of socks and my shoes, and walked downstairs where Megan was starting an aerobics video.

"There is nothing like aerobics to start a morning," she said with a smile on her face.

The workout was tiring but satisfying. I had never realized how tiring aerobics could be. I always assumed that it was just a light exercise that women did just to feel like they were dong a little exercise. After the workout, Megan made a health breakfast consisting of fruit juice that was just delicious. The shower that followed revitalized me, and I was now ready for whatever Megan had in store for me.

As I started to put on my white bustier, Megan walked in wearing a yellow sundress that made her look gorgeous.

"Are you ready for your first lesson how to be a girl?" she asked me.

"Sure. What do you want me to wear?

"Well, I thought that we should start with a lesson on women's clothing. It is very important for you to know what to wear. So, I was thinking about going into town and browse through the stores."

"Sounds like fun to me."

"All right then. Why don't you put on the fuchsia polo dress with a pair of sandals? Also, don't put on too much makeup since you don't want to look overdone."

I followed Megan's instructions and grabbed the polo dress out of the closet. I found my sandals, and used the vanity to do my makeup.

The drive to the mall was a couple of hours, and Megan filled me in on how to behave at the mall. She reassured me that nobody would notice that I was a guy underneath the clothes.

At the mall, Megan took me to shoe stores, lingerie stores, clothing stores, and at the end to the department store to the makeup section. At every store she calmly explained what to look for, and how to create an outfit. At the end of the trip, I felt confident that I could put together an outfit, and look wonderful. Besides all the learning, I ended up buying a pair of outfits, and Megan got herself a wonderful cocktail dress and a wonderful nightie.

As we drove home, I could not stop thinking about how much fun I had at the mall. Not only did I have fun, but also I managed to make it through the whole day without anybody making any snide comments at me. As a matter of fact, Megan noticed guys checking me out, and that just made me blush.

When we got home, Megan asked me if I was too tired for a little action. I told her to give me a minute so that I could go to my room get ready for her. 20 minutes later, Megan walked in wearing her new nightie, and holding a different rubber dildo, which I quickly identified as a vibrator.

Megan walked to me, and gently kissed me on the lips. She proceeded to move down my nightie, and found my panties with her left hand. She removed my panties and found my now hard cock and as she moved her head closer to it, she used her right hand to shove the vibrator up my ass. With my hole not being a virgin any more, the vibrator slipped in without so much pain. The orgasm that followed was like nothing that I had ever experienced. Megan's mouth worked swiftly on my cock, and her hand pumped the vibrator in and out of me. This resulted on me unloading a huge load into Megan's mouth.

As she finished licking me off, she stood up and kissed me again on the lips. This time her mouth passed on to me my own cum. She told me to enjoy it like a girl, not to swallow it all at once. As I enjoyed the salty taste of my cum, Megan continued to pump the vibrator into my hole. As soon as I finished my cum, Megan removed the vibrator and guided my head towards her cunt. With my head between her thighs, Megan instructed me as to how to pleasure her. As I worked my way into her cunt with my tongue, Megan began moving up and down until she climaxed. At that point she grabbed my head with both of her hands and held my head inside her cunt.

As her orgasm began to subside, we both went into the shower where we took a quick bath. The end of the second day of my weekend had come. I turned the lights off, and as I fell asleep I wondered what the next day would bring.

To be continued...


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