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.

Last summer was the best experience I had ever had, but it had to end some time. Mom and Jenny surprisingly didn’t catch on to anything that had happened, at least nothing that they mentioned to me. I had decided to go to a college that was close to home, but I wanted to live in the dorms as it was more convenient for me. It was definitely hard being fully on my own, but I was able to get through it.

During my first semester, I met my girlfriend Anna in a class that we shared. We bonded over our love for technology (both of us are Computer Science majors), and we began to date after a couple of months. I lost my virginity to her, and we have had sex a bunch of times since then. We love each other very much.

A couple months prior to the summer, I confessed my secret of crossdressing to her. She was really supportive, and she was actually excited more than anything. She’s bisexual, so maybe that had something to do with it? Either way, I’m really lucky to be with her.

As summer drew closer, Anna talked more and more about how she wanted to see me dressed as a woman. We decided that, once my mom and sister leave for their trip, we would start the process. She wanted to see the transformation happen before her eyes, so I wasn’t to do anything before she got there. While Anna was from out of town, she used the excuse of taking a short summer class to stay on campus, so she was going to be here for most of the summer.

This year, Mom and Jenny decided to go on a longer trip than normal. Jenny had just graduated, so she wanted to have one last hoorah before starting her new job. Mom had some extra vacation time built up, and she figured that this was the best time to use it. They decided on a whole month-long trip! That meant that I had twice as long to enjoy myself and have fun with Anna.

Day 1

Like last time, I helped take the suitcases to the taxi that was in front of our house. Mom and Jenny had a lot more packed this time, so it felt like there were bricks in their luggage. Mom gave me a longer hug than normal, saying she was really going to miss not seeing me for a while. She was a little worried that I would be bored out of my mind and couldn’t handle being alone for that long. I reassured her that I’ve done it before, and that Anna was around to keep me company. “She’ll be doing much more than that,” I thought. We gave our final goodbyes as they got into the cab, and it drove off.

Once the cab turned the corner, that’s when I texted Anna that it was time. “I’ll be there in about 30 minutes,” she texted back. The anticipation was killing me, I didn’t think I could wait that long. But soon, her car pulled up into the driveway. As she got out, I couldn’t help but stare at her. She was so gorgeous with her beautiful legs, sexy clothes, and perfect makeup. I still couldn’t believe I was dating her.

“Are you going to keep looking me over, or are we going to get to work?” she said, snapping me out of my trance. “Sorry, you just look so pretty,” I said. “Aww,” she blushed, giving me a peck on my lips. “Now, come on, I want to see you look pretty, too.” We walked back into the house and closed the door behind us.

We figured that the best way to start off was for me to take a shower. I stripped down and headed for the bathroom. “I’ll pick your clothes out while you’re in there. I guess your sister’s clothes are going to have to do for now until we get your own clothes,” Anna remarked. “My own clothes?” I questioned, but that was soon out of my mind as I got into the shower.

I took the bottle of Nair again and made sure that every inch of my body was covered with the cream. After a little while, I turned on the shower so everything would wash off of me. I touched my skin and it was back to being smooth. I was already getting hard from the erotic sensations, I’ve missed this so much. I cleaned the rest of myself with the feminine soap and shampoo and stepped out of the shower. I looked around the bathroom to see if there was anything that might make Anna happier, and I found a bottle of lotion. I used some of it on my skin and it made me even softer than before! I put on the dressing gown and left the bathroom.

On Jenny’s bed, Anna had just finished laying out the clothes for me to wear. There was a pair of pink panties with a matching bra (different than the set from last time), along with the breast forms. She had also put out a pair of short shorts with a light pink crop top.

Anna turned around and saw me for the first time with hairless skin. She smiled and said, “you look so sexy, especially with that dressing gown.” As I took off the gown, she could see that even the hair around my genitals was gone. “Mmm, I think I like you much better this way. But if we’re going to go all out, we have to something about your penis.” It was rock hard at that point, and tucking would be too difficult with it this way. Anna apparently knew what to do now.

She got on her knees and started playing with my penis. First, she stroked at a slow pace, but increased her speed gradually. Since I was already turned on, it didn’t take long for me to be at peak hardness. I was about ready to cum when she stopped. She waited almost a whole minute before taking my member in her mouth. She bobbed her head back and forth, with me loving the way her lips felt grazing my penis. She used her tongue to continuously heighten the sensations I was feeling, and soon I just couldn’t take it anymore. I cummed in her mouth like there was no tomorrow. She began to suck in order to get every drop of cum that was coming out of me, and my penis kept shrinking until it was just a little nub. That was the first blowjob I’d ever had, and it was amazing. Anna swallowed my cum and smiled. “Now you’ve got your own little clitty.”

Anna helped me tuck my now soft penis and had me slip on the panties. She picked up the breast forms, salthered some glue on them, and stuck them to my chest. She then took the bra and put it on me, easily hooking it behind me. I finished everything off by putting on the shorts and top. Seeing myself in the mirror, I smiled, knowing that this was just the beginning.

Once Anna had fully looked me over, she said, “Damn, you’ve got one hot body. Especially that cute little butt.” She then slapped me on my ass, and I think I blushed a little.

Before we started on hair and makeup, she got her suitcase out and opened it up. She then took out her own set of makeup, saying that it was probably better not to use my sister’s. She also took out a hair dryer, a curling iron, and some scissors.

Anna took the scissors and cut just a little bit off the bottom part of my hair. She used the hair dryer on my hair while she brushed it out a little. Once my hair was dry, she took the curling iron and used it to add a little style to my hair.

She announced that my hair was finished and we started on makeup. She gave me the foundation, mascara, eye shadow, and lipgloss, wanting to see me do it myself. Just like last summer, I took the foundation and applied it evenly to my face. I looked to the eye shadow, and the one Anna had for me was blue and glittery. I closed my eyes one at a time and applied the shadow to my eyelids. I then took the mascara and carefully used it on my eyelashes. Finally, I twisted off the wand of the lipgloss and covered my lips with the red color. I looked at myself, and I was breathtaking.

I then turned around for Anna to see my work, and she was shocked. “Baby, you look so sexy. I’m surprised you did that good of a job. I don’t think I can call you Leo anymore, you need a feminine name.” I thought about it for a little bit and said, “what about Lauren?” “Oh my god, that’s perfect!”

At this point, it was about 4:00 in the afternoon. “What should we do next?” I asked. “Let’s do a slumber party!” she practically blurted out, which is probably what she had planned from the start. So, with that, we moved to the living room.

First, we painted each other’s nails. She started off with painting my toenails in a bright pink color. She took some nail extensions out of her bag and glued them onto my fingertips. She filed them down into an oval shape before painting them with the same pink as my toes. Once my nails had dried, I did the same thing to Anna’s nails. Everything had become harder to do with my longer nails, but I honestly couldn’t complain. Soon enough, we had matching nails.

We felt a little hungry and decided to order a pizza. While we waited, we played truth or dare. I started off and said truth.

“How sexy do you feel right now?” Anna asked.

“Very sexy, a lot more than the last time I dressed up actually.”

Anna also chose truth. “I guess I’ve never asked you this, but when did you find out you were bisexual?”

“I was a little tipsy at a party in high school, and I made out with one of my friends. We then went into one of the bedrooms and did it, and it was the best sex I had ever had.”

“That sounds so hot.”

I then chose dare. “I want you to answer the door to the pizza guy once he gets here.”

“What? I don’t think I can do that.”

“Come on, you look completely like a girl, no one will think you are a boy. All you have to work on is your voice.”

I agreed, and she coached me on how to make me sound more feminine. I eventually got the hang of it. Once she proclaimed that I was ready, the doorbell rang. I hastily got up and answered the door. There was a teenage boy standing there with the pizza in his hands. He kind of stared at me a little before getting out, “Uh, cheese pizza, $7.50.” I hand him the cash and said, “here you go, and keep the change” in my new girly voice. I took the pizza, thanked him, and closed the door.

“Oh my god, Lauren, he was practically drooling over you!”

“If only he knew what I had tucked between my legs,” I said, and we both giggled.

As we ate our pizza, we talked about what the rest of the night looked like. Anna had the idea of watching a movie, but she wasn’t sure which one. I agreed with that idea. I took our plates and cleaned them in the sink.

Anna had gone to her suitcase and grabbed two matching pink babydolls, figuring that we should get comfortable. We both changed into them and snuggled on the couch. We found a chick flick and began to play the movie.

We only got about halfway through the movie before we were making out. The feeling of our lips touching, both of us with lipgloss on, was newly found sensation, and I was loving every minute of it. Once the movie ended, Anna suggested that we move to the bedroom.

I was about to take everything off before Anna stopped me. “I want us to have sex like women, no dick is needed.” I shrugged and we went back to making out, practically jumping onto my bed. I began to rub my pretty nails all over her body. I pinched her nipples, and she let out a moan. I then peaked my head under her babydoll to work on her nipples more. But now, I decided to use my mouth. I started to suck on her nipple and she moaned even louder this time. I swirled my tongue around and kept sucking, her moans being almost melodic. Then she let out a huge scream, and she cummed in her panties.

Knowing her, I knew she wasn’t done yet, so I moved my head down towards her vagina. I pulled down her panties, seeing how wet they had become. Keeping my hands up near her breasts, I began to eat her out. I played with her nipples while my mouth explored her opening. She was moaning even more than earlier. “Oooh, Lauren, I think I’m about to cum again!” Just as she said that, I could feel her spasming as her legs tightened around my body. One last twist of her nipples made cum fly out of her. After multiple spasms, my face was covered. I licked every last drop out of her vagina and went back up to kiss her so she could get a taste of her own juices. We then collapsed on the bed.

“That was amazing. I’m going have to return the favor to you sometime,” Anna exclaimed, still catching her breath.

This was going to be one hell of a month.

Day 4

“Hey Lauren, I think we need to go out and get you your own clothes.”

I wasn’t surprised that she brought this up again. I definitely didn’t want to keep wearing Jenny and Anna’s clothes, but I just didn’t think I could go out like this. I mentioned my concerns to Anna.

“I know this might be going a little fast, but I think you’re ready. You look nothing like a boy, and you’ve mastered your feminine voice. Worst case scenario, you will be seen a woman who’s just a little shy.”

She was right about that, and after a little more begging, I gave in. Soon, we left for the mall, and once we got there, I just felt butterflies in my stomach. This is such a big step, but I felt confident enough to step out of the car and walk inside with Anna. The mall was busy enough that day, so luckily nobody was paying attention to us. First, we went in Victoria’s Secret.

“You should pick out at least 5 matching sets, but there is probably more to get,” Anna told me.

“How much is all of this going to cost?”

“Don’t worry about it. My parents gave me a credit card to buy whatever I want.” I forgot her parents are rich, they own some big company on the east coast.

Since we knew my size, I didn’t have to try anything on (definitely glad about that). Once we were done in there, we had such a variety of items. There was panties (bikini, boyshorts, and thongs), bras (regular and sports), sheer pantyhose, and nightwear (babydolls and a nightgown), all in a range of reds, blues, and pinks.

We then moved on to one of the clothing stores. Anna didn’t say what I should get here, but she definitely veered me towards the more girly items. We soon had skirts, short shorts, frilly tops, and even a couple of dresses. This time, though, she wanted me to try on everything. We both went into one of the dressing rooms and I modeled everything for her. I actually was having fun, all of the nerves were gone at this point.

I got my original clothes back on and Anna said she was a little turned on from seeing me try on the clothes. We opted for a quickie as I pulled down her panties and fucked her with my pretty nails. We had both become extermely turned on from doing it in public, and she cummed twice, while I cummed once. We made sure our hair and makeup was still okay, stepped out of the dressing room, and paid for the clothes.

The shoe store was next, where I tried on too many shoes to count, all in varying heel sizes. We decided that I only needed a pair of sandals, some pumps, and a couple of high-heeled open-toed shoes.

The last store we went into was the beauty store. Anna said that I should choose my own makeup, she didn’t want to make an decisions for me here. I looked around a little and found two shades of lipgloss (red and pink), an eyeshadow palette, and some nice black mascara. Then I went to find some nail polish, which is my favorite thing to wear. I found a bright red, a baby blue, a light pink, a white, and base/top coats. I said that I was finished and we payed.

Before we left the mall, Anna mentioned she wanted to do some shopping on her own, but she wouldn’t be long. I said that was fine, and I would grab us some lunch. I bought a couple of light sandwiches from the food court and found a booth to sit at. After about 10 minutes, Anna came back from her shopping and we started eating.

“How did you feel about today?” she asked.

“It was good. I felt uncomfortable at first because I thought people would catch on to me being a guy. But after a while, I realized that nobody seemed to notice, or they just didn’t even care if they did notice.”

“I told you that you look like a woman, so I’m not surprised there weren’t any issues. But I think what also helped was the way you are moving now.”

“What do you mean?”

“Well, I think this might just be your heels, but you have started to sway your hips while you’re walking. And you have become more delicate when picking up things, probably because of your new nails.”

I guess I never realized it, but she was right. All of the things I was wearing forced me to change my movements, and I’ve been doing it enough for it to become second nature.

We finished up our meals and left the mall. I didn’t ask Anna what she had bought on her own, but she mentioned that it was a little surprise for me later in the week. I obviously didn’t know what that was, but I would soon find out that it was more than I would have ever expected.

I left off the story with me exploring my femininity with my girlfriend, Anna. We had gone to the mall, and Anna had bought a little something special for me…

Day 7

As I woke up, I noticed that Anna was lying awake in my arms. I kissed her and told her good morning, and she did the same. The combination of her closeness and the feeling of my new nightgown was exhilarating. This was definitely the life.

Anna was unfortunately leaving for a week. She was going back to her hometown to visit her family. I really wish she didn’t have to go, but I know how important family is to her.

Before we got up, Anna said that she wanted to give me a little treat for all of the effort I’ve put into becoming a woman. I got very excited as she pulled down my panties. She released my dick from its prison and it sprung to attention. She had me lay down on my back and she got to work.

She started by giving me a handjob. As she rubbed her hands along my member, her long nails would click and sometimes touch my skin. Her pretty nails could have made me cum on their own, but she kept the pace slow so that I didn’t explode too soon. She then took her hands off of me and lowered herself onto my penis. She moved little by little before I was fully inside her. I could feel her wetness with my penis, and it acted as a lubricant for our intimate love-making session. I was getting ready to cum, but she lifted herself off of my member before that could happen. She waited a little bit before she spoke.

“Before I let you cum, you’ve got to beg me for it like the girl you are.”

I was a little confused at first, but I understood. “I wanna cum sooooo bad.”

“I don’t know if that’s girly enough. I want to hear you talk about being a sissy and having your clitty sucked.”

“Please let me cum, my clitty is desperate to be sucked. I’m such a little sissy and need to have some release.”

“That’s better. Now keep saying it while I suck you.”

As she sucked on my dick, I cried out that I was such a sissy for having my clitty played with. I talked about how much of a girl I was and I was such a slut for wanting sex so much. Soon enough, my penis spasmed, and I began to cum in Anna’s mouth. Every little squirt was a wave of pleasure. She used her tongue to make sure that she could make me cum as much as possible. My dick became very small and was the same size as after the last blowjob. Anna, with cum still in her mouth, move up to kiss me. She released all my semen into my mouth and had me swallow. I still wasn’t a big fan of the taste, but in that moment, I did feel like a sissy slut.

Anna got up and grabbed something out of the shopping bag she had from our trip to the mall. Before I even knew what was happening, she took my dick and attached something to it. When I looked down, I saw a pink piece of plastic in place of my penis.

“This is called a chastity cage. It prevents you from getting hard or even touching yourself. I’ve got to make sure you stay a good girl while I’m gone. I’ll have the key with me, so there’s no way you’ll be able to get it off.”

I was a little stunned. Where the hell did this idea come from? I had to admit, it was more comfortable than the tucking, but still. I guess I was under her control at this point, and I just had to live with it.

We spent some of the morning hanging out before Anna had to get to the airport. I decided to drive her there in her car, since I didn’t want her to have to pay for a taxi or parking. Once we got there, we kissed each other goodbye. Before she went in, she mentioned something to me.

“I know you’re kind of disappointed about the little cage you have now, especially since you can’t masterbate like you normally do. But I couldn’t let you suffer, so if you get desperate for some release, I left a few surprises in my bag to help you do that. Bye, baby, I’ll miss you.” With that, she walked through the doors of the airport.

“More surprises,” I thought. “That’s just great. And how can I get release without having Anna and with my penis locked up?” I wondered what I had gotten myself into the whole time I was driving home.

Day 12

The first couple of days without Anna weren’t too bad. My nails had chipped a little, so I repainted them, with a French manicure on my fingers and red on my toes. I also kept practicing doing my makeup, even though I was already good at it. I tried on the clothes we bought last week again, making sure that I still liked them.

After a while, though, things got harder. With all of the feminine activities I was doing, I was getting horny. My penis would constantly try to get hard, so it kept straining against its cage with no luck, making me a little uncomfortable. At this point, I was feeling so hot and bothered that I couldn’t take it any longer.

I went to Anna’s bag to find what her surprises were. There was a bunch of things in the bag, but one of them had a note attached to it. It read:

Lauren,

I knew you would cave at some point, you little sissy slut. Since your penis is useless right now, you need a new way to get pleasure. This bag has many things for you to use, but I want you to start out with the toy this note is taped to. Use it on your virgin pussy, preferably while you’re on your back. There’s some lube in the bag, and I recommend using plenty of it. Have fun!

I looked at the toy and my eyes widened. It was a dildo! “I can’t use this, this is way too far!” I said aloud. But I started to wonder if it wasn’t. I was already completely like a girl in every way. During the past week, the way I looked, moved, and even had sex was in no way like a guy. Does that mean I should try to masterbate like a girl, too? I’ve been curious about what it’s like, and obviously Anna thought that I should try it out.

I was so horny that any worries were out the window. I took the dildo and examined it more. It was about 6 inches long and 1 inch wide. Could this thing really fit inside of me? I guess there is only one way to find out.

I stripped down to just my bra, grabbed the dildo and lube, and layed on my bed. I propped my legs up, with my asshole in full view, and got to work. I squirted some lube into my hand and rubbed it all over the dildo. I also used a little bit around the inside of my opening. I took the dildo and slid it in between my buttcheeks. As it entered my hole, I gasped. It was such a weird and wonderful sensation.

It didn’t take long for the dildo to be completely inside me. I slowly started moving it in and out, trying to mimic how I’ve fucked Anna before. I started to moan, it was almost involuntary. I soon found a spot that made me feel amazing and pumped the dildo so that it would consistently hit that spot. My moans were in line with the movements of the dildo. I kept at this pace for about 30 minutes before my body began to feel tingly. I rode this tingling sensation as it increased, and soon, my entire body was floating on a cloud. After a few more fucks of my opening, I felt a huge wave of pleasure rush over me, and I tensed up as I exploded with enjoyment. It felt almost like an orgasm, but different, and a lot more satisfying.

Laying on my bed, I still felt unbelievable. That was the best orgasm I had ever had, there was no doubt in my mind. Looking at my clitty, I noticed only a few drops of cum came out of me. All that pleasure, and I only cummed a little?

I realized that I still felt horny and decided to go at it again. Over the next hour, that dildo stayed inside me as I wanted to keep fucking myself. I orgasmed three more times over that time period. After the final one, I just collapsed on the bed. The dildo slid out of me on its own, making a distinct popping sound. I definitely had to do this again.

As I was getting up, I decided to see what else was in Anna’s bag. There were multiple dildos of various shapes and sizes, and one even vibrated. She also had an array of butt plugs in different sizes. I decided to see what they felt like and picked up the smallest one. I took a little more lube and squeezed the plug into my opening. “Ooh, that feels nice,” I thought.

I put my clothes back on and just chilled out for the rest of the day. I couldn’t help but tighten my sphincter every now and then, reminding me that the plug was still there. I loved having something inside of me. Anna was definitely right about me being a sissy.

Day 14

I drove to the airport to pick Anna up after her trip. As soon as she walked out, I got out of the car and greeted her. We made out for a little bit before I helped put her suitcase into the back of the car. People were probably a little weirded out seeing a “lesbian” couple kissing each other for so long, but I honestly didn’t care. We got into the car and drove off.

“Did you use any of the surprises I left for you?” Anna asked.

“I did. Actually, I’m using one of the butt plugs right now.”

“Mmm, I can’t wait to get back and see you with it. What about the dildo?”

“All I’ll say is my pussy isn’t a virgin anymore. I fucked myself silly the other day.”

“Oh my god, Lauren, that’s so damn hot. I think I need to fuck you later. I haven’t had any release all week, it was a little hard to do anything with my parents in the next room.”

Once we got to the house, we practically jumped out the car with excitement. After I closed the front door, we began to make out again. We took off each other’s clothes, leaving us in our sexy lingerie as we moved to the bedroom. “I wanna take a look at your pussy,” Anna exclaimed. “I need to know what I’m in for.”

I complied and took off my panties. I layed face down on the bed with my ass in the air. Anna smiled when she saw the butt plug, taking it in her hands and yanking it out. A little squeak came out of me when she did that.

“Before we get to it, I need you to do something. I can’t work with an unclean pussy, it’s unsanitary.” She grabbed something new out of the bag and gave it to me. “I want you to give yourself an enema. Make sure that the liquid that comes out of you is clear before you return to me.” I did as she said and came out with a nice, clean opening. “Now we’re ready.”

Anna had me get on all fours while she prepared herself. She played with my buttcheeks a little before spreading them out. She took some lube, spread it on her fingers, and got to work. She started by teasing the rim of my pussy before inserting one finger. She rhythmically moved her finger in and out of me before adding a second finger. I moaned with pleasure as she finger-fucked me as hard as she could. Once she added a third finger, I was in heaven. That small amount of effort made me orgasm in no time.

Obviously, we were still horny, so we weren’t done yet. Anna turned me on my back and moved her head towards my pussy. She was about to eat me out! She stuck her tongue out and got to work. It started out with just a light licking, but soon her tongue became its own fucking machine. Her tongue explored my pussy, and it consistently hit the sweet spot. I moaned even more than last time as she continued to devour me. This was amazing! I let out one last squeal before I orgasmed again.

“You up for more?”

“I’m still so fucking horny, of course I am!”

Anna got one of the dildos and used an attachment to strap it onto her. Looking at the dildo, it was about 8 inches long and 1 1/2 inches wide. God, that’s so big! “Now, this dildo is a little special, and you’re going to see why in a little bit.”

Staying on my back, I lifted my legs up onto Anna’s shoulders so she could have full access. She took a generous amount of lube and put it on the dildo and my pussy. When she entered me, I let out a little moan. It felt so good having my pussy stretched! She started with a slow pace and was only a couple inches deep. As time went on, she increased the speed a little, progressively getting the dildo further inside of me. Before I knew it, the whole thing was inside me.

I could feel an orgasm start to build up, but knew that it would still be a little while before it happened. I wanted this to be the best orgasm possible, so I said, “Fuck me harder! I want to feel everything!” Anna complied and quickened up the pace. I moaned with pleasure, and my moans began to sound more girly the more she fucked me.

We kept at this for about 10 minutes before I felt like I was going to orgasm again. “Oh god, I think I’m about to cum!” Right before the release, I felt the dildo jerk a little and something warm and sticky shot into my pussy. Whatever it was, it sent me over the edge. This time, as I orgasmed, a huge squirt of cum came out of me and hit Anna in the face. I was a little surprised by that, since I’ve only ever had a few little drops come out of me while locked up. We both collapsed on the bed, with the dildo still inside of me.

“I see you liked the little surprise this dildo had in store,” Anna said. “If you haven’t figured it out, it simulates the male orgasm and shoots out its own version of cum. So, you just got fucked in the most girly way possible.”

I was still catching my breath from that amazing experience. I honestly didn’t care that I practically had a penis cum inside of me. This newfound form of orgasm was life-changing, and I don’t think I ever wanted to go back to having a male orgasm.

Anna and I snuggled together in bed. I wondered what the rest of the month would be like as we fell asleep in each other’s embrace.

To be continued…