Ever since I was young, I was treated differently. My mom's friends would always comment on how pretty I was with my slender body, long eyelashes and bright green eyes. I spent a lot of time on my own growing up. My father left when I was a teen and my mom and older sister were always out of the house, which meant I spent a lot of time playing by myself.
When I was seventeen, I noticed that my body wasn't changing as much as my friends. I seemed to lack any manly characteristics and my penis size never really seemed to get any bigger. I thought this was normal until I went into a men's changing room after swimming and saw the other naked men.
I remember how intimidated I felt, changing among all the real men, their huge penises hanging between their legs. Their muscly arms and hairy bodies, how big and strong they all seemed compared to me. When I returned home that day, I stood naked in front of a mirror for a long time, looking at my body and trying to understand why I didn't look like them.
One day while I was home alone, feeling bored and lonely. I decided to play a game. I thought it would be fun to pretend to be a girl. I'd always played these type of fantasy games, imagining I was playing the role of a character in a movie, but this time I wanted to dress up.
I snuck into my sister's room and started to go through her wardrobe. I knew she had a long satin ruffled dress that she wore to a wedding once when we were younger and thought it would make me look more realistic for the part. I remember the feeling of the soft silk against my skin as I pulled the dress over my head and down over my naked body.
The excitement I felt as I tried on my first pantyhose and silk panties, the thrill of sliding my feet into a pair of chunky heeled platform heels and trying to walk like a girl. I looked in the mirror and noticed how different I looked, how much better I looked and felt dressed as a girl.
This continued for a few years, secretly dressing up and role-playing by myself, doing chores around the house while my mom and sister were at work until I left for college. I spent the first few months trying to fit into college life, making friends and trying to put my past behind me.
I never really had a lot of male friends but girls seemed to love me and would always want to hang. I was told I was a 'pretty boy' by a lot of women, and I guess that made most men jealous of me, the fact I received so much attention from women. The weird thing was, I never really knew how I felt about it all.
My best friend Leanne was fascinated with me. She would always flirt with me and we had messed around a few times, but had never let it go very far. She studied psychology and loved to talk to me about all her theories on men, which sometimes got very detailed and dirty, Leanne loved to dress super sexy when she went out and you could tell she knew the effect she had on men.
After sleeping with a guy, I would always hear about it the next day. She'd describe what they did, how he was in bed, his penis shape and size. Every detail. I would sometimes sit on her bed while she told me, looking at her rumpled clothes on the floor, the stains on her bed and imagine the sex in my head.
Leanne had no secrets with me and I knew everything about her. This only made my secret seem to grow even bigger, and made me feel really guilty about it. As time went on, I started to feel an overwhelming desire to dress again. I would watch Leanne get ready for a night out, picking out dresses and asking me which lingerie looked the most fuckable.
In my dorm room, I started to build a small collection of clothing I had "borrowed" from girls I knew, obviously without their knowledge. Leanne's friend Katrina once commented on how she seemed to have lost her favorite lace chemise and thought one of the other girls had stolen it. I just sat there, terrified that my secret might come out.
By the end of the third term, I had begun to spend more time in my room, dressing regularly again. It was coming to the end of the year and everyone just thought I was busy studying. Instead, I was experimenting with different looks and had begun shopping for clothes online.
I had become obsessed with the female form, the way women looked in magazines and adverts, and started writing an anonymous blog about cross-dressing. I had found a new friend online who commented on everything I wrote, leaving words of support, encouragement and advice.
I was still hanging out with Leanne a few times a week and she was now getting more interested in studying sexual behavior. Her latest subject was BDSM and fetishism. She would dress like a dominatrix and go to costume parties, collecting studies on peoples reactions.
She still told me everything that happened in her sex life, including the new experiences she was having which included threesomes, pegging and sex with girls. I lived vicariously through her for most of my college years, having only really had sex with a few girls my whole life.
She never asked me about my sex life but she always seemed to worry about me for some reason. Why I hadn't been dating anyone, if I liked anyone, what I was into? I always just told her I was fine and changed the subject to something else. Leanne was amazing, she always knew when not to push or pry and never made me feel uncomfortable.
My blog was becoming popular and I had built up a collection of photos of myself dressed en femme. I never showed my face out of fear I might be recognized, but even with just my body, I had built up a strong following of supporters. The best thing was that people seemed to love how I looked and would even send me messages asking if I was a real girl.
By the end of the year, I had moved on from just dressing like a girl, and was now spending most of my time alone practicing makeup and hairstyles, talking aloud in a female voice. I had learned how to move, how to walk and talk feminine. All the time alone had made me interested in sex as well.
I knew I enjoyed sex, and dressed as a girl, I would find myself more attractive craving to be more feminine. During my blog sessions, I would visit chat rooms talking about sex with people dressed as a girl! I went by Francesca online and people knew me by this name, which made me feel even more turned on.
During the day, I would wear lingerie under my boys' clothes and change back the second I was back safe in my room. I slept in silky gowns and baby dolls, sometimes with stockings wrapped around my legs. I began to explore my body further starting with my small finger slid gently between my legs, and slowly moving onto using my larger fingers.
I had made myself cum a few times from playing with me boy pussy, so the natural progression to masturbating with a vibrator didn't seem strange at all. After a while, the temptation mixed with the curiosity was enough to make me want to try sucking a realistic dildo, pretending I was giving a real blowjob.
I loved the idea of pleasuring someone in that way, the thought that I could be in control of the most sensitive part of someone. That I could be the sexy thing that made someone orgasm. I practiced sucking a dildo almost every night after that point, once again role-playing with my imagination.