Ellie's Journey Pt. 01


Could I do this? Could I live two separate lives? One as just a regular high school guy who gets no attention, and one as a girl who already has a date? Just last week I was staying home Friday nights playing video games.

"Fine, just this once to see how the other side is," I agree.

"Perfect!" Danielle says. "We will go to the mall tomorrow! Let's get some rest."


I woke up, laying on the floor next to Danielle and Kelly, on some blankets we had set up the night before. Both girls were still sleeping soundly. I stretched, and the tight clothes soon make me remember what all happened. I was still dressed as a girl.

I got up and went into the bathroom. I looked in the mirror, and didn't see myself, I saw a girl looking back at me. I turned on the water, cupped my hands under it, and brought it to my face. Looking up, some of the make up washed away. I studied the face in the mirror.

Who am I? I thought to myself. Am I still Alex? All my life, I had been a normal guy. Well, normal as you can be I guess. My parents were average people who made a decent income. My older sister and brother were both graduated and in college, making me the last child at home.

After a few short relationships and many missed chances, I've never done anything sexual. As I confessed, my first kiss was last night... with a boy, and it wasn't bad.

Subconsciously, I was too afraid to admit if I liked it or not. I'll worry about it later, I decided. I finished washing off my face, and returned to the girls' room.

As I walk in, I see Kelly on her phone, and Danielle still sleeping. "Hey, come over here," she whispers. I walk over to her and sit down by her on the floor. I look at her phone and see she has a picture of the mall layout loaded. "Okay, when we go shopping today, we will go to a few places to get everything you need!"

"How much are we getting? It's only one day!" I said.

"Well we have to plan for every occasion! We don't know what kind of date it will be! First we will go to Victoria's Secret, it's a must have for girls. Then we will go to Wet Seal, and Aeropostale. After that, whatever catches our eyes we will stop by!"

"I don't have that much money!" I admitted.

"Danielle and I are going to chip in, this is a fun experience for us too!"

"If you say so!" I said. I wasn't about to turn down free money, even if it was for a date with a guy.

After Danielle woke up, she and Kelly both showered. I showered last, and re-shaved myself smooth. This time was easier and faster. It almost felt good. I came back into the room with the bathrobe I used last night.

"Today since we will be walking around a lot, I think you should wear these!" Kelly handed me a pair of red tanga panties. They have a little more to them than a thong, but still have support like bikini cut panties. I grabbed them, and put them on the bed. "Now this bra should work fine for you," she said, handing me a red bra with white polka dots on it.

"We thought you should wear something that is stereotypically girly," Danielle said, "like a dress or short shorts. That way you can get used to the feeling, and it would be easy to change in and out of in the changing rooms."

"I don't know if I'm ready for a dress yet, so I guess we can try shorts," I said.

Kelly opened up a drawer and showed me a selection of short shorts. The selection was relatively similar, most being jean shorts. The only differences were the shades of color and one or two had sequence on the back of it. She pulled out a pair of medium blue shorts, and handed them to me. "Now for a top!"

After a few minutes of looking, we settled on a gray tank top sweater that cuts off at the midriff. We paired it with a light brown cardigan and we were ready to go.

I dropped the bathrobe and slid the panties up my legs. That indescribable sensation came over my body again as they came up. I tucked my member like I was taught, and made sure it was secure. The panties rode up a bit, and I could feel them hugging my crack, but it felt good. I had never experienced this feeling before. Then I put on the breast inserts, followed by the bra. The shorts came next. Once they were on, I felt like I still didn't have any pants on since they were so high. I felt a little bit of my butt hanging out of them. I then put on the top and cardigan.

Danielle and Kelly pushed me over to her desk and they did my make up for me. They put eyeliner on along with mascara and foundation. They topped off my look with some glittery lip gloss. I was almost complete. Kelly grabbed the wig from last night, and styled it so that I have some very nice curls to my hair. We were ready to go shopping for Ellie.

We all got in Kelly's car, and headed off to the mall. The leather seats were warm on my bare thighs, a new feeling for me again, but enjoyable one. We found a parking spot near the food court and walked in. Being a Saturday afternoon, the place was packed. We made our way through the crowded court into the main mall area. We kept walking until I could see it. The big pink sing saying "Victoria's Secret." Normally I would've hated going in here, but this time I was excited. We looked at each other and walked in.

We made our way straight to the panties section. There I had a choice between all the panties I could ever want or need. All sorts of colors and styles available to get. "You should pick out a few of each kind, so you can get a good feel for the styles," Danielle said.

I started going through the different kinds. I first went to the boy shorts, my favorite kind so far. I grabbed a pair that were pink with black lace trims, a red cotton pair with "PINK" on the back, and a blue and white striped pair. Next I walked over to the thongs. Since I haven't worn one yet, I decided I'd give a few a shot. My first pair were white ones with black hearts on them, followed by a bright pink lace topped pair, and an orange pair.

With these panties, I made my way to the g-strings. The thought of how they would feel free me to them. I quickly grabbed a blue and green pair, and added them to the pile. Lastly, I went to the bikini cut panties. I met Kelly there, and we picked out five different color cotton panties for me. With the panties taken care of, we moved onto the bras.

Kelly said, "we will buy you some bigger breast forms, so we will just get you some c cup bras for now, and buy that size inserts!" I nodded and we sorted through the bras. There were so many kinds and so many choices to choose from. I tried my best to get a few pairs that matched my panties. A red one, black, white, and blue. Then I saw some other ones a little bit over, so we walked there. Here, I grabbed a zebra print one, and one with hearts on it, along with a bra that had stripes on it. Lastly, we grabbed two strapless bras, just in case.

We went over to the PINK section of the store, and grabbed a few pairs of yoga pants and leggings. I also picked out a pink zip up sweatshirt. As we finished up here, Danielle said she'd meet up with us later, and left me and Kelly alone. We checked out and walked back into the main mall area. We walked over to the directory, but couldn't find wet seal at all. Suddenly, I felt a tap on my shoulder.

"Excuse me ladies, were you looking for a certain store?" The voice belonged to a 20 something old guy behind us.

"Yeah! We just can't seem to find Wet Seal on here!" Kelly said.

"Ah, see, I work here. Just go down left and it'll be in the right hand side!" He said.

"Thank you so much..."

"Steven. And it's no problem, anything to help two beautiful girls!"

I felt myself blush as we walked away. Did I just really get hit on, and pass as a girl?

"Nice job handling the pressure," Kelly nudged me.

After following his instructions, we found our way over to the store. Here, we were going to look for a few casual outfits. We went over to the jeans first. We grabbed a few different sizes, and went into the changing rooms. "Okay, so you're going to struggle a little with these like the other pair last night, but we have to get a perfect size for your body."

I slid on the first pair, and it came up too tight. After a few more pairs, we found the perfect size I needed. We came out of the dressing rooms and found many styles of jeans matching my size. We settled on a pair of light and dark blue skinny jeans, pink ones, and white ones. Satisfied with my jeans, we went to the shorts and picked out a few pairs of short shorts, in blue, dark red, black, and a sequenced pair. We then went to the shirts, and got a few t shirts and tank tops, along with two sweaters to go over some shirts in case it were cold outside. I also spotted a green army style jacket and added it to the cart. "I always thought these looked great on girls," I explained.

Lastly, we went over to the dresses. I was looking forward to this as I have never worn one before. Kelly explained I should get a few kinds, for many occasions. A sundress for a casual day, a tight party dress, and a stylish dress. We grabbed a bunch, and I went into the changing room. I stripped to my bra and panties, and got the first dress. It was a sundress, and not knowing exactly what to do, I just stepped in from the top and pulled it up. It hugged my top, but at the bottom, it was open and hung down to my knees. It was such an incredible and freeing feeling. I loved this, and I wanted more. I quickly got out of the sun dress and pulled up the tight dress. I looked in the mirror, and wow, I looked amazing. My usually hidden curves showed perfectly in the dress. I was hooked. I came out, and Kelly agreed too.

I decided to get a sundress that was white, with shoulder straps, and yellow flowers all over it that came down to my knees. For my party dress, I chose a black and white striped dress with an open back to it that hung just above mid thigh. And for my last dress, I chose a simple but elegant red dress that came down to my shins. We then went over to the shoes, and got me some black converse flats, and a pair of 3 inch heels that fit perfectly. Kelly said I would need a lot of practice with those.

Since we had most everyday clothes, we stopped into Aeropostale to get a bikini as summer was just around the corner. After looking at all the styles, I picked light pink bottoms with hearts on them, and a white top. I was ready to become Ellie. Or so I thought.

We got a text from Danielle saying:

We missed something, come over to the stores across from the food court.

Kelly and I hurried over there to see what we missed. There we saw Danielle, sitting outside of Flirt Boutique, holding some bags already. Once looking inside, it was easy to see it was a lingerie store.

"Why do I need this?" I asked, confused.

"Lingerie is what makes girls feel the most girly!" Danielle said. A quick glance around the store and I decided I'd give it a shot.

This store had everything you could think of. Stocking, garter belts, baby dolls, nighties, sexy underwear. There was so much to choose from. We got some black stockings along with a matching garter belt. A nice g string and bra came with the set. We also grabbed a white nightie. We were all done shopping for the day.

We made our way out of the mall and drove home. Once we got there, we brought everything upstairs to Kelly's room, and took out all the clothes. Feeling nervous but also excited for tomorrow, I went through and showed off all my outfits. Each one got thumbs up, and compliments.

We decided to leave most of the clothes at Kelly's house, so that my parents didn't ask any questions. They did however convince me to bring home a pair of leggings, a couple of panties and bras, a shirt, and my nighty.

I thanked the girls again, and walked home quickly. I entered my house, and three all the bags in the back of my closet. My parents wouldn't know any better, and I would be able to sneak on some of the clothes when I felt like it.

I started getting ready to go to sleep, but a strange urge convinced me to put on a pair of my panties before I fell asleep. I got up and put them on, then drifted off into one of the most peaceful sleeps of my life.

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