My name is Leo, and I am going to tell you the story of how I explored my feminine side.

My dad died when I was only 2. I was too young to even understand what happened, so I wasn’t really affected by his death. But my mom and my sister, Jenny, who was 5 at the time of his death, were heartbroken. The summer after my dad’s death, my mom decided that they would go on a girl’s trip for a couple weeks, as they needed a little break from grieving. After this trip, they decided that it would become a tradition to take place every summer. My story starts at the beginning of one of their trips when I was 18.

Day 1

I always love whenever my mom and sister leave for their trip. Having the house to myself is great, even though I don’t really do much. I helped Mom and Jenny put their suitcases in the taxi. They said their goodbyes, and of course, Mom said not to get into trouble, and everything else a mom has to say when leaving her kid home alone. They then got into the taxi and left for the airport.

The day started out like most days did whenever they are gone. I watched TV, played some video games, normal teen stuff. As time passed, I got a little bored, and decided to walk around the house. I was about to pass Jenny’s room, but I suddenly stopped. Jenny never lets me in her room, it’s practically forbidden territory. I hadn’t even thought about it before, and I decided that this was my chance to explore her room.

As I entered, I could tell that it was a very girly room. Pink walls, frilly pink bed sheets, and big closet full of clothes. The whole room was just really big. She even had her own bathroom, a luxury I did not have. I saw that she had a vanity with all of her makeup on it. Glancing at it, I saw her nail polish collection.

Jenny has always been a lover of nail polish. She has her nails painted 24/7, I rarely see her with bare, or even slightly chipped, nails. It always looks nice on her, and I personally think it looks hot on girls.

It was at that moment a thought popped into my head. “What would my nails look like with nail polish on?” I kind of shrugged it off because boys don’t normally wear nail polish, but curiosity got the best of me. It wouldn’t hurt just to see, right? The stuff can be taken off later, and I’ve got two weeks to myself.

Browsing through her collection, there was just so many. She had pinks, reds, blues, purples, you name it. I found a bright red that looked nice and decided on that. I started by taking off my socks to do my toenails. I shook the bottle like I’ve seen Jenny do many times, screwed off the brush, and got to work. Taking the leap into the unknown, I carefully applied the polish to my big toe. As the brush glided across the nail, I just felt a wave rush over me. It felt so good, so right. Once I finished that nail, I continued on and did the rest of my toes.

I observed my handiwork, and it looked amazing. The color was perfect, I didn’t think it would look this good. Every movement of my toes changed the reflection of light off of them, further reminding me of the polish’s presence. For some reason, the polish even made my feet look smaller, almost like a girl’s.

I then moved on to my fingernails. Pretty much the same process as my toes, just different nails. It was harder to paint with my non-dominant hand, but I was able to get the job done. After I finished, I took a look at what I had just done. Just like my toes, the polish looked really nice on my fingernails, and it made my hands seem smaller. The longer nails on my fingers made the nails look even more feminine than they already were. Looking at both my fingers and toes, I just couldn’t believe it. They were practically a woman’s feet and hands, but attached to me!

I soon noticed that my penis had become rock hard throughout the process. I knew what I had to. I checked to make sure my nails were dry and headed to my bedroom. I jumped onto my bed, and then I slid down my shorts and underwear to reveal my throbbing penis. I have masterbated plenty of times since hitting puberty, so this was nothing new to me.

I grabbed my penis with my newly painted nails and it was so hot. It was like getting a handjob from a woman, which I had yet to experience. I started slowly sliding my hand up and down my penis. It was so methodical seeing my feminine hand move that way, grasping my dick like it was taking on more than it could handle. The more I stroked, the harder my penis got, and it was soon standing attention like a flagpole. My eyes began to take notice to my polished toes and I couldn’t take it any longer. I exploded like I never had before, cum continuously squirting on my nails, stomach, and chest.

That was the most intense orgasm I had ever had. I had never experienced anything so mind-numbingly good. “This is definitely something I have to do more often,” I happily thought. I cleaned up after myself and went back to watching TV, nails and all. This was going to be a good couple of weeks.

Day 4

The first few days, I was doing what I normally did while the girls were gone. It was hard to keep my focus sometimes, though, I kept looking back at my nails. Just a glance at them made my dick spring to attention, almost every time. I masterbated so many times to relieve the pressure, but it barely did any good at keeping my penis soft.

This day, I again got bored and went back to Jenny’s room to see what else there was. I looked through some of her drawers and found pairs of panties. I hadn’t seen a pair up close before, I’ve only seen them on women in magazines and on the Internet. I grabbed a light blue pair in my hands, and they felt so soft. Why doesn’t my underwear feel this good? I was about to put them away when I paused. “These might be nice to wear,” I wondered, “but is this going too far? Nail polish is one thing, but panties are another level.” I thought about it, and I figured that I was getting to explore things I had never dreamed of, and when was there a better chance to do it?

I decided to go for it as I took off my shorts and underwear. I slowly stepped into the panties and slid them up my legs. The soft fabric felt so erotic touching my skin. This was like nothing that I had ever experienced before. Once the panties got into place, I noticed that they were a little tight due to my penis. I adjusted my member so that it was held in between my legs. It definitely feels better now.

Looking in my sister’s floor-length mirror, I was a little stunned. The panties looked so good on me. There was some noticeable hair on my legs, but I still looked very feminine below my stomach. The panties accentuated my butt and hips, giving my body some curves. I guess I never noticed the shape of my body since my boy clothes kind of hide it.

I decided to put my shorts back on as I went back to watching TV. Every time I moved, it reminded me that I had panties on. The softness of them was so comfortable, so much better than my normal underwear. The panties kept slipping in between my buttcheeks, and it made me feel so naughty. Once the day ended, I noticed that a little cum had dribbled from my penis onto the panties, and some of it went partially down my leg. I guess I had never realized it, I was too focused on everything else. I made a promise to myself that I would not wear boy underwear for the rest of my time alone, only panties.

Day 6

I went into Jenny’s room to change out “my” panties for the day. Before I did, though, I decided to take a look into Jenny’s bathroom. She had a big shower, definitely bigger than the one I’ve had to use. I looked at all of the products she had. There was the normal stuff, like body wash and shampoo, but with more feminine scents. There was one thing I didn’t recognize, though, and that was a bottle labelled “Nair”. On the bottle, it said that it was a depilatory to remove hair from your body, giving you silky smooth skin.

I’ve always kind of wondered what I would look like without hair on my body. Jenny always had hairless skin, I’ve only ever seen hair on the top of her head. It was a quick decision for me to slather the Nair all over my body. I waited the appropriate amount of time and jumped into Jenny’s shower. As the water came down, it washed all the cream off of me, my body hair going with it. My body felt so smooth, it was like silk, and it was erotic.

While I was in there, I cleaned myself up with Jenny’s body wash. Using her loofah, I washed every inch of my body. The flowery smell was very feminine, no wonder Jenny loves this stuff. I then used the shampoo to clean my somewhat-longer hair, giving it some shine and the same scent as the rest of my body.

Due to the scents and the whole experience, my penis was rock hard. I took my hand and started stroking, again loving how feminine my nails looked around my member. My other hand started feeling the rest of my body, and I got harder the more I touched my silky skin. It was an electrical feeling, stimulating the already sexy experience. My hand wandered up to my chest, and once my fingers grazed over my nipple, my body was jolted back. It felt like my nipple was connected my groin, with every little touch giving me an intense sensation. For a solid two minutes, I kept stroking my penis and tweaking my nipple. I was so desperate for release as the warm water from the shower ran down my back. I finally made one final tug on my nipple and it pushed me over the edge. My back arched and my body began to feel num. Cum erupted from my penis, every squirt flying through the air, with cum soon running down my smooth legs and onto my painted toes. I counted at least 20 individual squirts of cum as my dick got softer and softer. That orgasm was a lot more satisfying and much better than the one I had on the first day.

I made sure all the cum had washed off of me before stepping out of the shower. Jenny had a dressing gown hanging on her door, and I decided to wear that to dry me off while I picked out the panties I would use for today. I found a nice lacey red pair of panties that was a similar color to my nail polish. I slipped them on while still wearing the dressing gown. I loved the way it felt as the panties graced my now smooth legs.

I searched Jenny’s drawers to see if there was anything else to find. In one of the drawers, there was a bunch of bras. Curiosity took over and I decided to try one on. I found a bra that seemed to match the panties, and took off the dressing gown to expose my chest. I put my arms through the straps of the bra. I kind of struggled to connect the hooks in the back, but I was able to get it. Looking in the bra drawer, I saw a pair of something in the back. Picking them up, they felt like jelly, and some memories came back to me.

Jenny had worn these when she was younger. She was in a play before she had boobs, and they required her to have something on her chest to play the part. I had seen her get dressed for the play, so I knew what these were. They were fake breasts!

Since I had the bra on, I decided to see what I would look like with boobs. I inserted the breast forms into the cups of the bra, having to loosen the bra a little to make room for them. I cupped my hands around my new additions, feeling the weight that came with them. They were at least a B cup, maybe even more.

Looking in the mirror, I observed what I looked like. From the neck down, it was hard to tell that this was not a woman’s body. Like before, the panties made my waist and butt look very girly. The bra didn’t do much on its own, but the breast forms helped out there, making it seem as though I had real breasts. My body had no hair whatsoever, and I was probably just as smooth as Jenny normally was. If all of that didn’t make my body look feminine, my bright red nails made the difference.

I put my boy clothes over everything and decided to browse the Internet. I found that there are a lot of boys like me. I kind of thought I was weird for doing all of this, but knowing that I’m not alone made me feel a lot better. I wondered what else I could do to make my experience better…

Day 9

After doing a lot of research, I decided that I would fully embrace my femininity. Today I was going to see what it was like to fully become a girl. I was a little nervous, but I just had to explore my feminine side.

I started out by taking another shower. My body was still smooth from using the Nair the other day, I guess my hair just grows very slowly. I washed myself with the body wash and shampoo, and I really loved the flowery scent that they left on my body. After the shower, I got into the dressing gown again and got to work.

I started by working on my hair. My blonde-ish hair went down to my shoulders, so I had a lot to work with. I took Jenny’s brush and I parted my hair down the middle. I kept brushing my hair until it was completely straight. For the first time, I noticed that my hair looked very luxurious. The shampoo was really making it look nicer. I put some of Jenny’s curlers at the bottom portion of my hair, something I had seen Jenny do a few times. While that dried, I moved on to other things.

I was a little tired of my current nail color, the red got boring after a while. I took off all of the polish, and seeing myself with bare nails felt odd. I looked through Jenny’s collection and found a hot pink that I found to be very sexy. Once all of my nails, fingers and toes, were painted, I smiled as I loved the color.

Next, I decided to do my makeup for the first time. The past couple of days, I had watched a bunch of tutorials, so I was confident in my abilities. I started off with some foundation, which I spread evenly across my face. My sister and I have the same skin tone, so her’s works perfectly. Next, I took some eyeliner and carefully applied it, luckily not hurting my eyes in the process. I then took some mascara and used it on both sets of eyelashes. I looked through Jenny’s eye shadow, and found a blue and a pink that I thought would work well together. I first applied the blue, then blended in the pink to create a gradient effect on my eyes. Finally, I had some pink lipstick, which matched my nails. I took the lipstick and first colored in my lips, then I added a little more around them to make my lips look fuller and more feminine.

Once my hair dried, I took out the curlers. The curls of my hair looked so feminine, and every time I moved my head, they bounced. There was no doubt I had a feminine hairstyle now.

It was time to get dressed. I took off the dressing gown and my penis was standing attention. “I’ll have to do something about that,” I thought. I looked for a matching set of panties and bra to wear, and I found a pink set that looked nice. As I observed the panties, I noticed that there was a small opening in the back, placed right in the middle of my buttcheeks. “I wonder what this is for,” I thought, but I dismissed it, thinking it was some girl thing I don’t know about.

I slid the panties up my legs, getting the same electric feeling I have before. But before I completely got the panties up, I needed to do something about my penis. I had read about tucking online, and I knew that it would help me look the part. Using my pretty fingers, I shoved my balls inside me and used some tape to keep my penis in place. Only then could I fully put on the panties, since now I had a flat front. I took the matching bra, clasped it around my chest, and inserted the breast forms.

I search more of Jenny’s drawers and found what I now know is pantyhose. They felt really soft in my hands, even more soft than the panties. As I rolled the pantyhose up my legs, I felt a similar electric feeling as I did with the panties, but it was so much better, almost orgasmic.

I then moved on to Jenny’s closet to look for the clothes. This was the first time I had been in her big walk-in closet, and I was overwhelmed with how much she had in there. There were dresses, skirts, blouses, shoes, and so much more.

I found a short black skirt that looked nice, so I took it off of the hanger and slipped it on. It was so short that you could see my panties! I looked for a shirt to wear and saw a pink tank top that I’ve seen Jenny wear many times. I carefully slid it over my head as I didn’t want to mess up my makeup. I noticed that the tank top only went above my belly button. I finished the look off with a pair of tan wedges with 2-inch heels. It took a little bit to get used to walking in the heels, but I eventually got the hang of it.

I glanced at myself in Jenny’s mirror and I gasped. I didn’t see my reflection, I only saw a beautiful girl. The girl’s hair was long and elegant, with curls layered down towards her neck. Her makeup was perfect, her eyes standing out with the eye shadow and mascara, while her lips were in a feminine shape and color. Her boobs were very perky, almost popping out of her tank top. She had her luxurious legs encased in nylon, with her heels highlighting that her calves are to die for. Her nails, both fingers and toes, were perfectly painted and matched the rest of her outfit. She was my dream girl.

My penis was trying to break free from its prison as I got hornier and hornier. Oh my god, I was getting turned on by myself! I just couldn’t believe that I was the one in the mirror, and my penis obviously couldn’t tell, either.

I decided to take some pictures of myself. I took my phone and propped it on the floor next to the mirror, having it face Jenny’s bedroom door. I set it so that it would take a picture every few seconds and just let loose. I tried a variety of different poses, mostly ones where I’m laying on the floor. I took most of my clothes off for a few minutes to get sexy poses of me in just a bra and panties.

In one of Jenny’s drawers, I found a nice babydoll that matched my panties and decided to put it on. It had a bra built into it, so I didn’t have to worry about the breast forms falling out.

I posed for a few more pictures before a dirty thought came into my mind. I pulled down my panties a little and undid the tape that was holding my penis in place. I made sure that my member was in full view of the camera and started posing. I took positions of me doing a handjob, a footjob, and even going doggy-style, all with my enlarged penis being the main character. I could only imagine what these pictures looked like, a sexy woman playing with her penis.

Once finished with the pictures, I decided to take a video. I showed off my sexy legs, slowly running my painted nails across my smooth skin to meet similarly-painted toes. I squeezed my fake breasts, and even though I couldn’t feel anything, I arched my back to make it seem as though they were real and sensitive.

I took my penis in my hand and began to stroke it. I kept pumping and pumping for at least 10 minutes waiting for release, but it just wasn’t coming. Looking in the mirror, I could only see a sexy slut, one that was desperate to orgasm, and one that I wanted to fuck so badly. As I licked my lips, the woman in the mirror did the same, and all I could think about was those pretty pink lips sucking my cock, her tongue swirling around my member. It was at that moment I exploded with excitement. Cum flew everywhere, with the mirror, my legs, the babydoll, and even my face getting hit with the warm liquid. I was cumming for at least a minute before it finally stopped. I was shaking for a few minutes afterward, man that was amazing!

I licked a little bit of the cum off of my face as my sexy reflection did the same. It was so hot to look at, but honestly, I wasn’t a big fan of the taste of semen. Maybe it’s an acquired taste? I cleaned off everything of my sister’s that got hit with cum and wondered what I would do next.

I looked at the time, and it was only 12:00. I put my original outfit back on, retucked myself, and decided to grab something to eat. As I drank my water, it left a pretty pink stain on the glass, reminding me that I had lipstick on. I cleaned off my plate and noticed it was nice out. We had a pool, and I thought it would be fun to go for a swim. Our house had a tall wooden fence around it, so I could stay dressed en femme.

I looked through Jenny’s stuff to find some swimming wear. I found a pink two-piece bikini with a thong bottom and put it on. I also found a pair of feminine sunglasses that I might use. From her closet, I took out a set of Jenny’s sandals, which looked sexy on my feet. I grabbed a towel and headed outside.

I set all of my stuff down and jumped into the pool, making sure my hair stayed above the water as not to ruin it. Being in the water was definitely refreshing after the little session I had earlier. Swimming was a little harder to do with breasts, but I soon got used to it. Every kick of my legs made the thong bottoms slide in between my butt cheeks, and I felt giddy every time it happened.

After swimming for about half an hour, I got out, dried off, and relaxed on one of our lounge chairs. I put the sunglasses on as the sun was right in my eyes. I decided to tan myself a little bit, wondering how I would look with bikini tan lines. I flipped over after a while to get my backside, and soon after that I decided to head inside. While changing out of the swim clothes, I looked at my skin, and it was very obvious that I’d had a bikini on, especially around my chest.

I redid my makeup a little, since the pool messed it up. For the rest of the day, I tried on a lot of Jenny’s clothes, taking pictures along the way. She had a bunch of dresses, ranging from long and modest to short and skimpy. I even tried on her light blue prom dress, along with silver heels, and I just couldn’t get over the fact how hot and pretty I looked.

Her shoe collection was amazing, there was so much variety. I started out small, trying on flats, sandals, and flip-flops. Then, I began to wear every pair of shoes one by one, going from minimal heel all the way to seven inches tall. With every increase in heel size, I practiced walking in the shoes for a while, and soon heels became no problem for me.

Time must have flew by for me because it was no sooner time for dinner. After kicking off the shoes I was wearing, I put on some of Jenny’s yoga pants and a sports bra, then headed to the kitchen for a light meal. After eating, I looked up a few yoga videos and exercised for over an hour, similar to what Jenny did every night. I then relaxed on the couch and watched some TV.

A couple hours passed and I was feeling really tired, it was such a long but enjoyable day. I went to Jenny’s room, changed out of my clothes, and put on the same babydoll that I wore during my masturbation session. I decided to sleep in her room because why not? Her satin sheets, along with the babydoll, rubbed against my smooth skin, and it was so erotic. I think I was leaking a large amount cum in my panties, as I noticed a wet spot on them. My dick was soft the whole time, even after I had untucked myself earlier, and I didn’t even know that much cum could come out without being hard. I’ve heard that women get wet without any stimulation down there, I guess this is something similar? I then fell asleep, knowing that this was a perfect end to the best day ever.

Day 13

For the last days of Mom and Jenny’s trip, I had lived as woman, and it was an incredible experience. Now, though, I had to go back to boy mode, as they were coming home the next day.

I first changed into my regular clothes, which kind of felt weird, a little uncomfortable I might add. I looked at my face and did the work to make sure I got every last trace of makeup off. I took the nail polish off of my fingernails, and was going to do my toes, but I figured that I could keep them a secret. I brushed my hair back to its original style, getting rid of my curls. My body hair was starting to grow back; I didn’t have much to begin with, so I figured that a couple more days would bring it back to normal. I noticed my tan had almost gone away, but it could still be seen a little, so until it was completely gone, I could hide it. Finally, I cleaned all of Jenny’s clothes that I had worn, along with making sure her room was exactly how she had left it. I also ended up downloading an app on my phone that requires a passcode to see specific photos and videos, and transferred everything I took over the course of these past two weeks into it.

For the rest of the time I had, I just watched some TV, but it made me reflect on what I had done. Did this mean I was gay? “I don’t think so, I’m definitely still attracted to women, and the thought of having sex with a man sounds gross,” I thought. What about being transgender? Do I fully want to be a woman? “While that might be fun temporarily, I love my penis, and I don’t think I would want a vagina to replace what I have already.”

What does this mean for me, then? I guess I could be described as a crossdresser, but it wasn’t necessarily about looking like a woman: it was the sexual thrill that I felt when being like one. I don’t think there’s a great term to represent my situation, but I don’t really care. All that matters is that it was fun and there was no harm done.

I kicked me feet up onto the coffee table to see my pretty pink toes. I’m kind of sad I have to hide these, but I’ll still get to see them at least once a day. And I have my pictures to look at, so it’s not like this experience is just running around in my brain.

Day 14

Mom and Jenny got out of the cab and we greeted each other with hugs. I helped them unload their stuff and bring everything inside. I asked how their trip was, and they said it was fun. They asked what I did the past two weeks, and of course I lied and said just video games and TV. Mom joked and said that college was going to bite me in the butt come next month.

We ate dinner as they talked about what they did on their trip. They went to beaches, hit up bars, and did a lot of relaxing. I couldn’t help but think what it would be like to go on the trip with them. I guess I would have to be a girl for two weeks, but it’s not like that would be much different than what transpired at the house.

We sat on the couch and watched a few movies together before calling it a night. I almost went to Jenny’s room on instinct, but I stopped myself and made sure that didn’t happen. I entered my room, changed my clothes, and got into bed. As I fell asleep, I was a little disappointed that it would be a while before I could dress up again. But I was still excited for what would happen, and I couldn’t wait for next year.