Ellie’s Journey Pt. 01

Nis 27, 2024 // By:analsex // No Comment

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This story contains parts 1-3 of my Prom series, that I have been working on. I decided to change a few parts of it, edit it a little, and slightly change the direction it was headed to one I could agree with better. I hope you still enjoy this story as I continue to write it!


It was mid April, and the school year was winding down for us seniors. Classes were about studying for the finals and the homework was getting easier. I had just turned 18 in December, but no big changes had happened like I assumed automatically would. Little did I know some events were going to take place that would change who I was.

I had some friends, not many, just a few close ones, guys and girls, who I hung out with. Now, since I wasn’t a ladies man, I became best friends with a few girls at my school. 2 in particular, Kelly and Danielle. We had been friends through middle school, and always have been close. Even as legal adults now we still talk about cartoons and video games. We even lived close by, only a few blocks away from one another. Due to that fact, I would walk home with them everyday.

Today was a Friday, and as soon as the first bell rang, I went to my locker and dropped off my books. Kelly came over to me. “Hey!” she exclaimed.

A bit startled, I turned around and said hi back. We chatted about our day as we started walking to Danielle’s locker. We quickly pick her up and carry on the conversation as before. Eventually, they start talking about girl things as I slowly drift into the back of the group. We exit the school and start walking home. I hear them talking about prom, and who they hope asks them, and their dresses and so on. I, on the other hand, get carried away in watching the girls walk ahead of me.

Kelly is much shorter than even me, about 5’1 and is beautiful. She has long flowing light blonde hair and bright blue eyes. For her size she has an impressive bust of c cups and a nice tight butt. She also has a very good sense of style.

Danielle is taller, around 5’7 with light brown hair to the middle of her back. She often wears leggings or skinny jeans, which is great because she has an amazing booty. Her feminine figure is almost perfect in every way.

I’m quickly snapped out of my daze when I feel a raindrop hit my face. The girls seemed to notice too. We hurry up out pace and make it to Kelly’s house, the first stop. The rain keeps coming down harder and harder, and by the time we reached her house, we were soaked.

“You guys can stay here till the rain blows over!” she says. Obviously, we agreed as the rain starts coming down in buckets.

We made it inside Kelly’s house and headed to her room upstairs. I’ve only been in her room a few times, and it was briefly at that. She has a queen sized bed and nice white dressers and nightstands in her room. Along one wall is a closet filled with tons of her clothes. “So what should we do since we have some time together?” Danielle asked.

“Well I want to go see that new movie out in theaters! You know, the romance one? I can call up a guy I’ve been talking to and he can bring a friend for you!”

“That sounds great! But what about him?” They turned and looked at me. “He’s soaking wet with no clothes to change into.”

“It’s fine! I mean I could just run home quick. I don’t wanna ruin your girls night!” I said.

Danielle pulled Kelly to the side and started whispering to her. A few moments later, she says, “what if you joined us? We never really get to hang out with you anyways! This’ll be a fun time!”

“I would, but really, my clothes are soaking wet. I can’t sit in a theater like this.”

“Well, since it is a girls night, how would you like to borrow some of my clothes?” Kelly gleams.

“Uhh, what?” I stammer.

“Yeah! It’ll be fun! We can turn you into a really convincing girl!”

“How far are we talking?” I ask hesitantly.

“You have to do it all or you won’t be convincing!” Danielle explained.

“I’ll try it, and if I don’t like it I’m stopping. Got it?”

The girls squeal together. “Deal!”

“Okay, first things first! We need you to shower clean and shave your body hair!”

“All of it? What if people will see?”

“That’s the point! And yes all of it because we don’t know which outfit you’ll be wearing!”

I sigh. “Fine..” And I headed to the bathroom. I close the door behind me and turn on the shower. I took a moment to think about what I’m about to do. I decided there is no going back, especially with these two in control. I undressed and got into the shower. I looked around as I let the water wet me down. I found the razor and the shaving cream. Starting from the bottom, I shaved up my leg. After a few minutes, my left leg is completely smooth. It feels weird, not having anything there, but also nice. I quickly shaved the other leg, my butt, chest, and crotch. For the first time, I’m completely smooth. I grabbed a towel to dry off in and step out. The cold air sent shivers down my freshly shaven body.

I grabbed samsun escort a bathrobe that was hanging up, and made my way back to Kelly’s room. The girls saw my shaven legs from about knee down, and gave me a nod of approval. They quickly turned back to Kelly’s opened laptop. I peeked over their shoulders, and see instructions with images.

“What’s all this?” I ask.

“It’s going to help us hide your dick from your panties! It’s called tucking!” Danielle explained.

They go through explaining how to push the testicle up and taping everything back. I enter the bathroom and perform the task. I looked in the mirror and was quite surprised to see no penis, but only a small bump. Barely any tape was showing. I put the robe on and returned to the room.

“Okay! So now, you get to choose your first pair of panties!” Kelly excites. Laid out on her bed, were many styles and colors of panties. I saw all from thongs to boy shorts to bikini cuts. I made my way over to the boy shorts, figuring I should have some extra support for my first time. I picked up a pair of black panties, with black lace around the edges. The only color was a pink bow in the front.

“I love your choice!” snickered Danielle. I was quickly thrown a black matching bra. I started to head for the bathroom to change, but was stopped. “You can just change here! We are all girls here!” Kelly persuaded. I shrugged my shoulder and figured my package was hidden anyways. I slide up the panties.

A feeling passed over me like nothing I felt before. I felt amazing to have my ass cupped like that. The tightness of the panties caused my member to strain again the tape, but it held. Kelly helped me put on her bra. “Here, you can use these! I had to use them in dance class when I was a kid and not fully developed yet! She hands me two B cup breast inserts to put on. The attach onto me and are held firmly in place. The added weight feels odd, but also good.

“She’s really starting to come together, huh Kelly?”

“We haven’t even started!” Kelly threw open her closet, and a bunch of clothes same into sight. She grabbed a pair of blue skinny jeans, along with a red, tight fitting top and a tank top. “These should do well to give you a good look, but also hide your man bits!”

I pulled the skinny jeans on, and after a minute or two of struggling, I got them on. In the mirror, I saw myself, and saw how much my butt really does stick out. It’s almost like a girls butt. I pulled the tank top on and the shirt over that. Danielle helped me straighten everything and my outfit was complete.

Next was the makeup. Kelly sat me down in front of her dresser and started holding up various types of makeup to my face to see what matched me. After a few minutes, she decided on a few pieces, and went to work. She put eyeliner on my eyes, and mascara on the lashes. Then she covered up my face with some foundation, and put on some eyeshadow for me. Lastly, some light red lipstick. “Maybe some day you’ll learn to do this yourself! she said.

During this time, Danielle was digging through Kelly’s closet and found a long black wig. “How do you feel about this one?” she asked.

“It’s perfect!” After a few minutes of straightening it and combing it, it finally sat right on my head.

A few minutes later, a car horn beeped outside and we headed downstairs. Kelly says, “Oh by the way, you’re name is Ellie for tonight.”

As so begins my journey as Ellie.

We start to walk down the stairs, and it’s then I first realize how different these clothes feel. I mean, sure, putting them on was a way different feeling than what I was used to, but the way the panties hug my butt, and the way the jeans made me sway while walking. I felt strange. But also sexy. Could this really be happening to me? A few days ago I was just a normal guy, who enjoyed watching football, playing video games, and listening to music. I never put this much time into an outfit, not even for other school events, why was this so different?

Sometimes when I went to social gatherings with friends like a bonfire or party, we’d talk about why being the opposite gender would be so much better. Girls get more attention and free stuff, guys have more work, is what my guy friends would say. The girls would say they had to deal with the guys always staring at them, which I could never understand why that was a problem. I’d love to be checked out and talked about always! Them again, I never really had the “look” high school girls wanted in a guy.

“Hurry up, Ellie,” Kelly shouted. “You still need shoes!” She handed me a pair of black and white flats to put on. “It’s weird how you seem to fit in most of my stuff! Maybe we can go shopping together!”

I wanted to say no, that this was a one night thing, but so far I enjoyed this experience. I managed out a “yeah, maybe.”

Usually I hate shopping, but something about this feeling had me intrigued. We open the door, and a cool breeze hits us. I feel escort samsun it blow on my chest, a feeling I never had before as all of my guys clothes are crew cut. This new feeling sent shivers down my spine.

Out in the driveway is a blue car. The driver and passenger sides open and two guys step out. The driver walks straight over to Danielle and the hug each other. He introduced himself as Dave. He was about 5’10 with an athletic build, blonde short hair, and blue eyes. Later on I found out he’s a soccer player for a neighboring school district. The other guy went over to Kelly and introduced himself as Alex. Alex was smaller at 5’8 with brown hair and brown eyes, but and more muscle on him than Dave. Alex played football for his school.

As we were walking to get in the car, the back door opens, and out comes another guy!

Dave says, “oh, by the way, we invited Mitch to come since your new friend is coming! That way she isn’t left out!”

Kelly and Danielle turn to me and give me a look of apology and confusion. Kelly whispers to me, “just go with the flow, nothing happens on the first date.”

He slowly walks over to me. “Hey there! I’m Kevin, nice to meet you…”

“Ellie,” I force out, not being used to that name yet.

“Nice to meet you, Ellie. We will have a great time tonight, don’t worry!” We all climb into the car and drive to the movie theater.

One the was there, the car was full of teenage awkwardness. Small talk would pop up here and there, and then silence, even between the other “couples”. After about a half an hour, we arrive at the theater. We start walking in, and I reach for my wallet, realizing it’s not there. I have a mini heart attack until I remember it’s in my guy jeans at home. The feeling of women’s clothing started to feel normal on me. I almost forgot I was Ellie.

I walk closer to Kelly and tell her my dilemma. “Don’t worry! I bet Kevin planned on paying for you anyways! Girls always get free stuff!” She giggles.

We approach the counter, and the guys all go first, ordering popcorn, soda and tickets. Once Kevin goes up, I go up with him.

“Two tickets for theater 6 please,” he asks the cashier.

“Are you sure? You don’t have to pay for me,” I say.

“It’s no problem! Since you’re my date I have to! Plus you don’t have a purse, and I wouldn’t want to know where else you keep your money!” He gives me a smirk and a playful nudge. “Come on, let’s go have fun.”

The six of us walked into the theater, and sat in a row, dates next to one another.

During the movie, I barely payed attention. Most of my time was spent thinking about what I was doing, what would happen, and if Kevin would try anything. If he did, what would I do? I’m certainly not gay, and I’ve never wanted to be with a guy before. I excused myself to use the restroom, and Kelly quickly followed. Thankfully she did, otherwise I would’ve walked straight into the men’s room. Once inside she confronts me. “Hey, is everything okay? I haven’t seen you look at the screen for more than 5 minutes at a time!”

“I’m not gay Kelly, I can’t do this! And I just don’t know how to feel right now. Being treated so nicely just because I’m a girl is amazing, I love this feeling. And these clothes are sorta turning me on. If I wasn’t tucked, you could certainly tell I’m a guy.”

“Well, what do you think of Kevin?”

“He’s nice. I don’t know, he treats me really nicely and I like his look and.. And I’m only saying this as Ellie, but I think he’s kinda hot too.”

“I thought you weren’t gay,” she jokes, jabbing me with her finger.

“I’m not. But dressed like this, feeling this way, I can’t help it.”

“Well listen, Danielle and I won’t judge you at all. In fact, this is our secret, so we won’t tell anyone what happens. We are like your best friends. Now the movie is almost over, and after we can come back to my house and talk about all of this, okay?”

I agree, and we head back for the remainder of the movie. Kevin asks if everything is okay. I smile and cheerfully say everything’s great.

As the movie ends, we all get in the car and head home. Kevin helps me out of the car, smiling all the while. “Thanks for paying tonight,” I shyly mutter.

“No problem! That means next time you have to!” He laughs. I did have a good time tonight, and I was wondering if I could get your number?”

At this point, all three couples we in their own conversation, and no one was watching us. We sit there in silence for what seems like an eternity. I figure since he goes to a different school, no one there could find out. I give him my number.

“Thanks! I’ll be sure to text you soon! And thanks again for tonight!”

“I had a good time too, I admit.”

“Well goodnight Ellie, maybe I’ll see you around?”

“Maybe. Have a goodnight Ke-” my sentence gets cut off by Kevin’s lips on mine. I don’t move, but slowly melt into the kiss. Why am I enjoying this? I shouldn’t samsun escort bayan be.

A million similar thoughts are running through my mind when he pulls away. “Goodnight Ellie, he says, and gets back into the car.

We walk back into the house and close the door behind us. “What was that? Huh, Ellie?” Danielle smirks.

“It was my first kiss.”

“You’ve never kissed anyone before?” Danielle asks.

“No, you guys know I never had a real serious girlfriend before.”

“Well did you like it?” questioned Kelly.

“I think he did! He, or I should say she, never pulled away!” She pointed out. “If you didn’t like it, you would’ve stopped it. Just saying”

“I guess it was kinda nice..” I admitted.

“Come up to my room! We can finish talking there!” We all climbed the steps and entered her room. Kelly hopped on the bed and invited us over to sit down. There’s enough room because it’s a queen sized bed. We gather around and chat.

“So what happened after the kiss?”

“I just gave him my number, thinking no one would recognize it from his school.”

“What if he calls or texts you?” Kelly questioned.

“I guess I’ll play along. I don’t HAVE to go on dates with him. I’ll just tell him I’m not interested and disappear. I mean, I can’t be Ellie forever.”

“Would you want to? How did you feel?”

“Well I like the attention you get, and the special treatment. Those are some big pluses. And the clothes do feel nice, but I can’t let people see me like this.”

“Well since me and Danielle are spending the night here, why don’t you join us? We can get you some more clothes since yours are still wet!”

“Well it is a Friday, and I have nothing going on…”

“So it’s official! Ellie is sleeping over!” Danielle squealed.

“Do we really have to call me that?”

“Well you look like her, so yes,” Kelly winks.

“What do girls all wear for bed?” I asked nervously.

“Whatever is comfy! I wear leggings and a tank top,” said Kelly.

“I wear shorts and a tank top too!” said Danielle. “You can pick whatever you want!”

They pulled me over to the closet again and showed me all the lounging clothes. From athletic shorts to leggings to sweets. “I always have found leggings to be sexy,” I admitted.

“Leggings it is!” Kelly threw me a pair of black leggings and a black tank top to go with it.

“I’ll go change quick!” I said, starting to leave the room.

“Change here, remember silly!” Danielle said.

Disappointedly I walked back in, and began to undress. I took off my shirt followed by the white tank top under it. I then struggled with the skinny jeans, but managed to get them off. Looking back up, now only in a bra and panties, I see the girls smiling. I asked what’s so funny.

“Looks like someone had a good night!” Danielle remarked.

I looked down to see what they are looking at. Where my private was tucked, a wet spot could be seen. I started to stammer a bit.

“Don’t worry, I’ll get you some new ones! Kelly walked over to her panty drawer and dug around. After a minute she came back. “We don’t have any more boyshorts for you, would this be okay?” She held up some light blue bikini cut panties.

I assessed how well they should keep me secure, and agreed. I slid them up my legs, and felt the same sensation run over my body, but a different one this time. It felt weird, but also nice, around my butt. The panties slid right into it, giving me a unique sensation. I then pulled up the leggings, feeling the warmth and comfort of the tight clothes. No wonder girls always wear these, I thought. They feel so relaxing, like it’s a hug for your legs.

Now feeling comfortable, I went back over to the bed. “I think I’ll get ready too!” said Kelly. She went over to her closet and grabbed a pair of leggings and a white tank top. To my surprise, she dropped her pants right in front of us, showing us her purple thong. She pulled up her leggings and proceeded to remover her shirt and tank top. She turned around, and unclasped her bra, then pulled the tank top over herself. With me still in some shock, she comes back over. “Don’t be so wooed! We are girls, remember?”

“I’m, uh, I’m, sorry..” I muttered.

“I’ll get changed too!” Danielle said, and walked over to her bag. She pulled out some yoga shorts and her tank top. Removing her bottoms, a solid white thong was presented to us. She then slid up her shorts which beautifully cupped her ass. Then, she took off the top and bra, threw them in the bag, and put her tank top on. “There! We are ready for the night!”

We gathered around on Kelly’s bed, almost in a circle. Just as Kelly was about to talk, my phone buzzed. I went to reach for it, when Danielle swoops it out of my hand.

“Hey, this is Kevin. I had a great time tonight and was wondering if you could hang out Sunday?” she read. After a few seconds of typing and pushing me back, she sent a text confirming the date.

“Why did you do that?!” I exclaimed, frustrated.

“You need to expand your horizons. Just go on one date, so you know how it is!” Danielle explained.

“What am I supposed to wear now?” I asked, still upset.

“Let’s go to the mall tomorrow!” Kelly added. “We can get you a few things and just keep them in my closet for when you aren’t Ellie!”

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