Finally Getting to be Myself

From the earliest possible moment one can know, I knew I was meant to be a girl. The problem is, I was born with a male body. I don't remember how old I was. But I knew that I had a lot more in common with girls than with boys.

I grew up in the late 90's and early 2000's. And where I lived, there was a lot of homophobia. The insults "gay" and "faggot" were thrown around a lot. Any excuse, and the guys would jump all over you. If you got those labels, your life was going to be very rough. You would be constantly harassed, bullied, and if things went the wrong way, you could get beaten up, or worse. An example, there was a suspected gay kid in a high school math class I was in. One day, the straight guy sitting in front of him, leapt out of his seat in the middle of class and screamed at the top of his lungs, "SHUT THE FUCK UP YOU FUCKING FAGGOT! I HOPE YOU GET AIDS AND DIE!" The sad part is, that kid didn't get in much trouble at all. That was the world I grew up in. I'm thankful we've come so far since.

So, you can imagine that knowing I'm a woman in a man's body, was not something I could risk acting on. I picked that up very early too. I spent my school years pretending to be something I'm not, a jock and male. Thankfully, I was born with a good amount of athleticism. I played every sport except football. So, I was lucky, I could blend in. But I always knew where I really belonged. I wanted to be with the girls. I wanted long hair. And to do my nails. And to go to slumber parties. And wear makeup. And chase boys. I wanted it, but I knew I couldn't get it.

I'm not French. I'm not a hat person. But one of the crystalizing moments in my life was walking down the street in New York City one winter (I grew up in the suburbs just outside NYC), a pregnant woman walked past my family, and she had a beret on. To this day, she's the only person I've walked down the street and turned and looked at. She just oozed femininity! I saw her and thought, "that's everything I want to be!" And since then, berets were my silent admission of who I am. Yes, berets can be worn by men and women, but in America, if you go to any online shop, or at the time, department store, if they sold berets, they were in the women's section. Unless you're in the military, or are a well-established artist, berets are seen as women's hats. I bought my first one at a secondhand store (Prince's song came out before I was even born, I hear guys say "raspberry beret" to me a lot) which was black. Then I learned how I could get things on amazon, so I bought 2 more on the DL. One was red. One was light pink. I could never wear them in public since I didn't want anyone to know about my sexuality. But they were my silent form of acknowledging who I am.

Thanks to teen comedies like American Pie, when I was in high school, everyone was having sex. Freshman, sophomores, juniors and seniors. I don't want to speak for the rest of the country, but that's how it was where I lived. If you hadn't lost your virginity by the time you were a senior in high school, it was seen as something was wrong with you. Not saying it's right or wrong, but it's how it was where I lived. And I wanted to do it myself. There was just one major problem, finding a guy who could do it, and wouldn't talk about it.

I would sometimes put a beret in my backpack when I was in high school. I knew if it was discovered it wouldn't be great. But I thought the odds were low on that one. On this particular day, I put my light pink one in my backpack, stuffed at the bottom so there was no chance of anyone seeing it. It was actually pretty late in the morning when our principal announced that we were going to have a half day because of some incoming snow. Because my car was in the shop, for the first time in a while, I had to take the bus home.

The bus ride was fine, if awkward. Nothing like going from having your own car and being independent to having to take the bus with the younger kids from high school. I didn't look in the back when I got on, I was embarrassed enough. My stop was the last one on the bus. My neighborhood was pretty empty during that time of the day. So when I got off the bus, I thought I was safe for a few moments. If cars or people were coming, I'd be able to see them. I reached down into my backpack and grabbed my light pink beret and put it on my head.

I had taken 2 steps when I felt a hand on my shoulder from behind, and heard a male voice say, "that's cute." Immediately I was horrified! I had made a massive mistake! I was exposed! Whoever it was would tell my parents. Probably rumor would spread around school. I turned around and whipped my beret off all in one motion, terrified that someone had seen me, and desperate to make sure word didn't spread. It turns out, that male voice was a guy I sort of knew from my neighborhood named Alex.

Alex was pretty cute. At the time, he was around 6 feet tall, but for a bigger guy, he was very clumsy with his body. He wasn't athletic like me. "Sorry if I surprised you! I thought you knew I was here." He said. "That hat was a joke. I was wearing it because some of my friends dared me. It's not mine." I said in a total panic. A smirk came across his face. "Don't worry about it. I actually thought it was kind of funny. You can put it back on if you want. I won't tell anyone." I could see that he meant it. That he wasn't thinking of humiliating me or exposing me. There was a kindness in his eyes. What meant so much to me, meant nothing to him. "I was actually going to ask if you wanted to have some lunch at my house." Curiously, I did put my beret back on. And seeing that his offer looked genuine, I actually took him up on it. His house was a shorter walk in our neighborhood than mine was.

I put my bag down as we walked through the front door. My first hint that he had something in mind was when I went to take off my coat and my shoes and beret and he told me to leave the beret on. It struck me as a little odd but, it wasn't enough to stop me. We went to his kitchen.

"Make yourself anything you want. I'll be right back." Alex said as I looked around his kitchen. I found a can of tuna and some mayo in the refrigerator, along with some bread in the pantry, so I made myself a tuna sandwich. I turned around to bring it to his kitchen table when I saw Alex standing there, holding up one of his older sisters' skirts. It was light pink, the same shade as my beret. I was excited, but he could be setting me up, so I had to act like I didn't want it. "What's that for?" I asked. He looked disappointed and lowered it a little. "Come on, you're wearing a pink beret. You don't have to pretend." Again, the thought that he was setting me up, getting me to do something girly only to pull back and make fun of me went through my head. It only takes one bad decision and a few seconds to ruin your reputation. "I told you; my friends dared me. I'm a man of my word." Alex looked disappointed and walked out of the kitchen. I heard him go upstairs at a quick pace.

I sat there at his kitchen table for a little while. I took a couple of bites of the sandwich I had made. I wasn't sure if I should just get up and walk out. I was both super nervous and intrigued at the same time. Alex came back downstairs, this time with even more. He still had the same skirt, but this time he brought a blouse and panties. He could see that I was still going to say no based on my expression. "You don't have to worry. I promise, I'll never tell anyone if you put them on. There's just as much risk for me as there is for you." I got the sense that he meant it. I was still unsure, and he could see it. "Come on. You're wearing that pink hat because you want to. You wore it because you thought no one was around. You weren't wearing it around your friends to hold up your end of a dare. You don't have to worry. If you want to wear these clothes, I'll never tell anyone."

I sat there frozen for what felt like minutes, but it was probably just a few seconds. I knew this was a major decision. Things could go wrong at any moment. I still felt like any second if I said yes that he would start making fun of me or take a picture to send it around school. I couldn't come to a decision really, but somehow, I blurted out, "ok." I could see the smile grow on his face, which again, made me nervous. I still felt like I was walking into a trap somehow. I took the skirt, white button up blouse and light pink panties, and Alex showed me to a bathroom where I could change.

I don't think I've ever been more excited, and I don't think I've ever been more nervous. I had worn some of my Mom's clothes before, but that was for a short time when I had my house to myself. And here I am, in someone else's house, putting on his older sisters' pink panties, then the blouse which I then tucked in to the skirt. I put my beret back on and looked at myself in the mirror. I felt pretty. I wish I had longer hair and makeup, but this was what I could do. Alex knocked on the door, "everything ok in there?" he asked. "Yep, just finishing!" I said back. I took three deep breaths and threw open the door. Alex was standing there, and he looked really amused. "You look really cute!" he said. I exhaled a little. There was no camera. No one jumped out to surprise me. Things seemed to be ok. I put my male clothes in my backpack by the front door, and we walked back into the kitchen where my sandwich was still sitting there, untouched.

I offered him some of my sandwich, but he didn't want it. So, we sat there at his table, I slowly but surely eating and Alex sat across from me. "So how does it feel?" I started to feel really shy. My dream was coming true. I was wearing women's clothes, sitting across from a somewhat handsome guy. But I still felt super shy. "It feels pretty good." I said as I took another bite. I could sense some unease in him as I looked at him. He seemed restless and fidgety. "So your sister left these behind when she went to college?" I asked. "Nope, she's home for Christmas break. But she got a job in town to make some extra money. I'll wash everything before she gets home. Don't worry!" Alex said. I kept taking small bites of my sandwich, trying to get a read on the situation. Alex kept looking anxious and fidgety.

Finally, after what seemed like a while, I couldn't take it anymore. I had to know. I looked right at him, "are you ok? You seem a little jumpy?" that's all it took. Alex leaned across the table and gave me a quick kiss on the lips. Again, the first thought that hit me was that he was trying to set me up. I pulled back. I had kissed a boy before, but so far as I knew, Alex was straight. He kept looking at me like he wanted more. "Are you sure?" I asked in a whisper. He leaned across the table and kissed me again. This one wasn't quick. This one had passion. And tongue. We made out for what felt like half an hour. I can't really say as I wasn't looking at any clocks.

After that, he got up from his side of the table and came over to my side. He put his hand on my thigh and looked at me. "You're dressed like a girl. Can I treat you like a girl?" I could see he seemed genuine. As I was thinking, he started to slowly unzip his fly. I kept looking at his eyes. Then down at his bulge. Then back up. I wasn't sure what to say. I wanted to say yes. But I was still very nervous. He pulled out his beautiful penis. It was long and hard. The head was beautiful. And it was standing straight up from his pants. I kept looking at it. Alex got my attention and looked me right in the eyes. "If you want, you be the girl. I'll be the guy. If you want..." that's all it took for me. I wanted that penis. I lowered my mouth on it and started sucking it right away.

This was not my first time with a penis in my mouth. But I never wanted one more. I felt so girly and I loved it! Up and down I went on his beautiful penis. Each time I would get back up to the head, I'd flick my tongue around it to give it a little extra feeling. Alex put his hand on my head as I went up and down on his cock. It was such a perfect size and shape! I could hear him breathe in hard and exhale. He seemed to be enjoying himself. And I knew I was! After a few minutes of his cock in my mouth, after a really deep breath in, I heard him say, "hold on!" I thought I had done something wrong, so I came back up very quickly. I was looking at Alex, and he didn't seem upset. He looked very satisfied. But he hadn't cum yet. I couldn't help but wonder why he wanted me to hold on.

Alex stood up and held out his hand. I stood up and he pulled me close and we made out again. Alex pulled away and looked me right in the eyes, "Do you want to go all the way... as a girl?" "YES!" I basically shouted at him. That was all it took. He turned me around and bent me over the kitchen table right next to my half-eaten sandwich. He pulled the panties down and lined up his beautiful cock. We were young and stupid, and hadn't given it a lot of thought. We hadn't considered lube or anything like that. Alex tried to enter me and he pushed hard. But it wouldn't work. He tried spitting on his cock, but that didn't get us anywhere. We needed some lube. Alex looked around in the kitchen, but we couldn't find anything that seemed like a good idea. He went into a bathroom and came out with some Vaseline.

He put it all over his penis and a little on my hole. He pushed and the head popped in. It hurt so badly! "TAKE IT OUT! TAKE IT OUT!" I screamed. Alex pulled out very easily. "Are you ok?" he asked me. I was terrified! Here I was, my first time, and his penis hurt me. I was so scared. What if I wasn't meant to be a girl after all? What if I couldn't have everything I wanted? I was not happy at all. I caught my breath, and Alex kissed me as I was still bent over. "Do you want to try again?" he asked me. "Yes" I whispered back. Hoping the second time would be better than the first.

He put a little more Vaseline on his penis and put it at my entrance, and pushed. This time was totally different. My hole relaxed and his head felt good. I could only moan in approval as I felt my body start to get overwhelmed by this new feeling of a cock inside me. "Go slow" was all I could manage to say as he slowly pushed himself inside me inch by inch. Until finally, his hips were resting against my butt and he was all the way in. The last thought I had before pleasure overtook my mind, was "YES! I'M HAVING SEX AS A GIRL!"

He was slow and gentle to start. A nice slow pace so I could get used to it. Each time he pulled back and pushed in, a wave of pleasure would go through my body. Starting from his cock, it would radiate through me. It was the greatest pleasure I've ever experienced. As I got more used to the intense pleasure I felt, he would pick up the pace. Alex told me later I was moaning so loudly he was worried the neighbors would hear. I really can't say, as my mind was blank, and my body was in heaven as the feeling of his nice cock fucking me. The only thing I remember is that Alex would lean over me and whisper in my ear, "You're the faggot. You're the one taking it in the ass." I could care less, as I found the whole experience overwhelming in the best way.

I could feel him picking up the pace. "I'm close." He said after a little bit. I don't know if we did it for 10 minutes, or 10 hours. I lost track of space and time. All I could focus on was the intense waves of pleasure going through my body. We were both breathing heavily. Finally, I heard him yell, "I'm going to cum!" the next thing I knew, he was pushing himself in as deep as he could. I felt a warm sensation in my belly as he came in me. In that moment, I was in heaven. I was wearing a pink skirt, white blouse, pink panties and a pink beret. A guy was penetrating me like a woman, and I got him to cum inside of me. I had never felt more girly and happier! I was breathing hard with my eyes closed, trying to catch my breath.

"WHAT'RE YOU DOING HERE!" I heard Alex scream. It scared me but Alex was still draped on top of me. Standing right there in the doorway to the kitchen from the garage, was Alex's older sister, Christina standing there looking right at us! I dropped my head right away, and she didn't see my face. "Dude" she said, "it's ok if you want to have some fun! Just do it in your room!" I could hear her walking towards us. Alex and I remained frozen, and I think she could sense something wasn't normal. "So who is the lucky lady?"

That's when I raised my head and she could see who I am. She looked at me and realized. Alex stood back and started saying over and over, "it's ok! I was the guy!" I could feel the tension in the room. I was frozen with fear. Not only did she see me in the outfit (which was mostly hers) I was wearing, she saw me bent over, with her brother's cock in me. This was the most serious breach of security. I pulled the panties up and ran for the bathroom, forgetting my own clothes. Just hoping to get somewhere where I couldn't be seen.

I got to the bathroom, and my head was spinning. Christina and I didn't really know each other. She was 2 years older. We used to take the school bus when we were younger, but I don't think we ever really spoke to each other. I could hear their muffled voices in the bathroom. I could hear Alex say, "please don't tell anyone!" And I heard Christina say, "You don't have to worry about that. I just had no idea you liked guys." "I don't" Alex said, "I was tricked and guys are going to do what guys do in that situation!" "Tricked?" Christina asked, "so when you discovered there was no vagina and you kept going, you were... tricked?" I could hear her giggle a little bit. Alex had no answer. I heard Christina say, "Don't worry about it. You're fine. I'll never tell anyone. Why don't you put the rest of your clothes back on and collect yourself. I'll talk to your lady."

That was not what I wanted to hear. I was shaking with nerves in the bathroom. Thankfully, I still had her clothes on, so I wasn't naked. I didn't want to talk to anyone. I wanted to get my clothes back on and run out of that house as quickly as I possibly could. There was one major problem, my clothes weren't near me. They were still in my backpack by the door. I wasn't sure what to do. Whether I should yell to not talk to me. Whether I should make a run for my bag and just run out the door and change somewhere quiet and private. I just froze.

Knock knock knock I heard, followed by Christina's voice, "hey in there! It's ok! I'm so sorry about what happened. I promise I'll never tell a soul! You can do whatever is most comfortable for you, but would you mind opening the door?" I stayed in the bathroom sitting on the toilet. Totally unsure of what to do. I couldn't find words to answer her. It felt like a few minutes went by when she knocked again. "it's ok! Us ladies stick together! Our parents will be home soon! I know it's overwhelming! And you're probably scared. But if you don't want things to get more complicated, it's a good idea to open the door for me." I realized there was no secret way out of the house. The only way was for me to open the door and go from there.

I opened it slowly. Christina was standing next to the far wall, giving me a little distance. As I stepped out, she said, "pretty. I can see why my brother went for it." Those small words of kindness kind of snapped me back into the present. I looked up at her, and I think she could see how terrified I was. "Don't worry" she said, "I'm totally on your side. I've known gay guys in high school, and one of my best friends in college is gay and he borrows my stuff sometimes." That really helped me calm down again. "Plus," she said as she looked me up and down, "you can keep the clothes. I definitely don't want those panties back!" she looked into my eyes and giggled. That made me giggle a little bit too. I didn't feel threatened. I actually felt safe.